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I finally provided my tax details to my accountant yesterday. As I expected, there won’t be enough time to work out the details before today’s tax filing deadline, so I’ll be filing extensions. In years past, when I filed for myself and my taxes were simpler, I usually waited until the last day. My procrastination has been helped by the availability of online filing. I’m thrilled to no longer need to run to the post office late at night on April 15. (This year, the deadline is April 17 due to a holiday in D.C.) In recent years, I could just as easily fill out the paperwork and file in my pajamas without leaving the house, even from the comfort of my own bed with a laptop computer.

The last few years, my taxes have grown more complicated, and my accountant now has me in the habit of filing an extension every year. This gives me six extra months to file my paperwork, a task getting increasingly complicated, having moved from an employee with only W-2 income, to a “part-time” self-employed individual with some income recorded on W-2 forms, some on 1099 forms, and some on no forms, to the sole owner of a business filing with an S-Corp status, with K-1 forms in addition to 1099s and W-2s, to an even more complicated situation in 2011.

Filing a federal extension for your personal taxes is free and simple. Before you get started, find your previous year’s final tax return (or just your adjusted gross income amount) to verify your identity with the IRS. Make sure you know your other personal information, like Social Security number, and have the information from your W-2 ready.

Step 1. Visit the IRS-sanctioned website, Free File Fillable Forms. Popular tax filing software programs also offer customers the ability to file for an extension. With the IRS-sanctioned website, you can be sure that the service will always be free and you won’t be distracted by advertisements for paid products. As of today, it’s free to file an extension using TurboTax, but there is no guarantee that this method will be free on the day you want to file your extension.

Step 2. Create your account. Whether you use the Free File Fillable Forms website (hereafter called “FFFF” for brevity) or commercial software, you’ll be required to create an account or login to an existing account. If you’re creating a new account, select a user name that will be easy to remember. With FFFF, you’ll have the opportunity to print your account username and password for reference.

Step 3. Select the appropriate form. With FFFF, you have the choice between forms 1040, 1040A, and 1040EZ. You’ll need to select the form that’s right for you. Form 1040 is the most comprehensive choice, so it is always safe. Depending on your situation, you may not be able to file your taxes using forms 1040A or 1040EZ. Keep in mind that you can still use TurboTax, H&R Block, or any other software to file your taxes before the extended deadline. Even if you file your extension using FFFF, you do not need to return to the IRS-sanctioned website to finalize your tax return. For example, I filed my extension via FFFF myself, but my accountant will be filing my tax return later this year using the method of his choosing. If you plan on finishing your return using some other method, just choose Form 1040 here by clicking the “Start 1040″ button.

Step 4. Complete your personal information. Begin by entering your information at the top of form 1040. Include just your name, address, and Social Security number. At the top right of the screen, there is a button labeled “EXT” that looks like the image included here. Click that button (on FFFF, not here).

Step 5. Estimate your tax liability. Here’s the problem with filing for an extension: the IRS won’t extend the deadline for paying any tax that you owe. Only the paperwork receives the extension. If you haven’t paid your full tax bill, you may owe money. You need to estimate how much total tax you owe for last year’s income. On the form, you will then subtract your total payments, including withholding from your job. To avoid having to pay any penalties, your total payments must be 100% of what you owe. I added up all the payments I made, included withholding from my former day job, the amount of last year’s overpayment that I applied to this year’s taxes, and the estimated payments. Since I paid more than my estimated total liability, I did not need to make a payment when filing for the extension.

Step 6. Complete the form. You’ll need to select a PIN, enter your birthday, and consent to the disclosure statement.

Step 7. Pay your tax liability. If you’ve determined in Step 7 that you need to pay when filing for an extension to avoid a penalty, you have a few options. You can print form 1040V and send a check to the IRS, or you can provide your tax filing service, whether FFFF or a private software company, with your banking information. The IRS will pull the amount you specify from your account electronically using direct debit.

Step 8. Submit your extension. Once all the information is complete, the “E-File Extension Now” button will be available at the top of the page if you’re using FFFF. With other software, you will be prompted to file your extension paperwork at the end of the process, though in some cases, you might need to pay a fee. You’ll receive responses through email twice. The first will come as soon as you submit your form to notify you that the extension has been submitted to the IRS. Within hours, if there is no problem with the information you entered, you should receive a second response to notify you that the IRS has accepted your extension paperwork and you will now have an extra six months to file your taxes.

Don’t forget to look into filing an extension for your state taxes as well. In New Jersey, where I live, this is easy. I do not need to file any paperwork in New Jersey for my personal extension. When the IRS grants an extension for federal tax returns, New Jersey will automatically allow the later deadline. If I didn’t pay enough state taxes throughout the year, I would need to pay the state when filing for the extension, just like I would need to with the federal tax extension. When I file my paperwork later this year, I can include a copy of my federal extension form and the state will not penalize me for filling late. Different states may operate differently, so always verify what you need to do before the initial tax filing deadline.

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How to File Your Taxes for Free

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The federal government can only operate with the help of the millions of individuals who earn income in this country and dutifully pay taxes. You would think that, in order to ensure a smooth revenue stream of considerable size, the IRS would make filing taxes as easy and painless as possible. That’s obviously not the case, considering the tax code is one of the most confusing human inventions on the planet today. The IRS does ensure that filing federal tax returns is completely free for millions of Americans with the help of a select number of software companies, provided the taxpayer meets a few eligibility requirements. If you can file your federal taxes for free, do so. There’s no point in spending unnecessary money.

If your taxes are complicated, and you require a professional to review or complete your forms, or you require some features not available in the free editions, then go ahead and pay for software or pay a professional. For the cast majority of Americans, free e-filing is a great option.

Starting with the most popular software companies, here are the best options for filing your taxes for free. I’ve updated this list for 2011 returns filed in early 2012. The deadline is April 17, 2012.

TurboTax Choose EasyTurboTax Online. TurboTax tops the list because they are fast to adjust to tax law changes, it’s part of a large company that has a strong reputation for personal finance, and there is a large user community for peer-to-peer support. The TurboTax Freedom edition is free for e-filing if any of these criteria apply to you:

  • Your adjusted gross income (AGI) is $31,000 or less, or
  • You are active military with an AGI of $57,000 or less, or
  • You qualify for the Earned Income Tax Credit (EITC)

I’ve used TurboTax in the past, and here is a TurboTax Online review as of the latest version of the software. For 2011 returns filed in 2012, TurboTax has lowered the maximum AGI for filing for free, reducing the availability of the program. If you live north of the border, you’ll need to access TurboTax Canada.

Save 25% on H&R Block At Home Online ProductsH&R Block. H&R Block’s primary business is in seasonal storefronts where taxpayers can bring their financial documentation into a specialist to work through the forms in person. The company also offers the “At Home” filing service for those who like the do-it-yourself approach. While the company normally charges for federal tax filing, if you use the At Home service and meet the following condition, you can e-file your federal taxes for free.

  • Your adjusted gross income (AGI) is $57,000 or less, and
  • You are age 52 or younger

Here is my review of H&R Block’s software, updated recently to reflect the changes since last year. H&R Block has also lowered the maximum AGI, but to a lesser degree than TurboTax has, and because the IRS has stipulated that $57,000 be the maximum AGI, though companies are free to set a lower maximum. In other words, this is the highest maximum allowed by the IRS.

Free TaxAct. When TurboTax was no longer free for me, and before moving to an accountant to handle my business, I was still able to e-file for free using TaxAct. TaxAct doesn’t have the brand strength or the large community of the two above software services, but the calculations are correct and the system that guides you through your calculations is just as complete. You can e-file your federal taxes for free using Free TaxAct if the following conditions apply.

  • Your adjusted gross income (AGI) is $57,000 or less, and
  • You are between the ages of 19 and 55 inclusive

eSmart Tax powered by CompleteTax. To e-file for free, your AGI must be less than $57,000 and you must be age 52 or younger.

TaxSlayer. TaxSlayer offers free e-filing for taxpayers with an AGI of $57,000. You must be age 25 or younger, be active in the military, or be eligible for the Earned Income Tax Credit in order to qualify for free federal e-filing.

Other free e-filing options are limited by the state in which you live in addition to other limitations similar to those above.

The deadline is approaching fast, and maybe taxpayers wait until the last possible minute to file. I suggest starting as early as possible, once you have all the information you need, to ensure you don’t encounter any delays or glitches. I have never heard of there being any software problems at the last minute, but it’s better to be safe than owe penalties to the government.

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If you’re interested in theater and have money you don’t mind losing, you may consider expanding your horizons by investing in a Broadway or off-Broadway show. Be prepared to lose money, though, because according to a variety of producers, only one show in five breaks even.

When a play or musical is in the planning stages, producers seek out investors to cover the costs of getting the show to opening night. After the show opens, income from the box office should pay for operating expenses. Any positive cash flow after expenses is distributed back to investors until their initial investments are paid back in full. Any profits after investors are repaid their initial investment are distributed back to the investors and producers, 50 percent to each (in the United States). Some shows never make a profit, but if you’ve backed a hit, you could see healthy returns, comfortably beating the stock market.

Broadway showFor the most part, individuals who wish to invest in theater, due to the risky nature of the business, must be accredited. The investor’s household must have a net worth of $1 million or more, excluding primary residence, or income of at least $200,000 ($300,000 for a married couple) for the past two years. There are ways to invest as a non-accredited investor, but the competition is higher for these opportunities because producers are limited in the number of non-accredited investors they can accept.

While the average investment from an individual is $20,000 to $25,000, you can often invest with $10,000, and sometimes with as little as $5,000. This minimum investment is lower than some mutual funds. The bigger the show and the higher probability of its success, the harder it would be to find an opportunity to invest at these lower amounts.

Ken Davenport, a Broadway producer with experience working closely with investors, took this concept of attracting smaller investors even further. When producing Godspell, Ken took to the streets, accepting investors with as little as $1,000 as a minimum investment. Investors received billing outside the theater and the chance to profit. With the play opening late last year and with the show not exactly being the hottest ticket in town, some investors in ken Davenport’s group, “The People of Godspell,” have reported that they’ve received checks towards paying back their initial investment, though the show seems to be far away from profiting for these investors.

The pioneers of attracting smaller investors to Broadway are Richard Frankel, Marc Routh, Thomas Viertel, and Steven Baruch. This team has produced seventy-five shows, and if an investor had invested $10,000 in each opportunity since 1985 through 2009, he or she would have received an annual rate of return of 27%, compared with the 7.29% of the S&P 500.

If you are not interested in Broadway or the dramatic arts, you may want to avoid investing due to risk. While financial reward is what all investors are seeking, investors in theater often look for intangible or invaluable returns. Producers will often offer investors a chance to be a part of the show, like attending opening night performances and after-show parties with the cast and creative staff, access to house seats, and in the case of Godspell and it’s pool of smaller investors, your name on a poster. For some, these benefits make investing worthwhile despite the risk.

If these benefits are not appealing to you, you may be only focused on the return of an investment, and stand to be disappointed if the show you back is like four out of five shows that never turn a profit.

Similarities to investing in the stock market. Just like a mutual fund, the best returns are reserved for investors who make the best decisions. Assuming you’re familiar with theater in the first place, you may want to become familiar with the production team’s track record before handing over any money to a show. While investors in the stock market may diversify across a variety of investments in an attempt to smooth out the peaks and valleys of investing over time, diversifying among a number of shows could be difficult. There may be only one show a season you find worth your investment, so your diversification must cover a long stretch of time.

Differences to investing in the stock market. When you invest in the stock market, you can do your research from your bedroom. You can read financial statements in the comfort of your own home, transferring money electronically to your bank account to your investment when you’re ready to purchase a stock or fund. All the information you need is available without leaving your house.

Investing in theater is more like investing in a company directly with a major financial commitment or receiving a substantial share of ownership. Before you make a major investment, giving you a substantial stake in a company, you’ll want to meet the executive team, analyze the financial documents, and handle more of the due diligence in person. When investing in a Broadway show, much of the information you need is not available online. You can use the Theatrical Index to look at every active production’s gross receipts and you can use the Internet Broadway Database to verify information about producers and productions, but it’s best to meet the producers in person, learn about the production, and determine whether you believe the show has the potential to succeed.

Early investors in Rent made a fortune; investors in Spider-Man: Turn Off The Dark probably won’t receive their initial investment back until the show has been running for four years, if it survives that long. Despite it being the most expensive Broadway show ever put into production, Spider-Man seemed like a safer bet, with a big name producer and a widely-recognized brand.

If you’re interested in getting started, here are a few suggestions.

  • Ken Davenport’s introduction is a good place to start.
  • Consider signing up for the Theatrical Index newsletter (linked above) to have access to financial information.
  • Find producers you’d like to work with, and send them introductory letters via email. Even if the particular producers you’re interested in are not currently looking for investors, you will be on their list to be the first to know when they’re seeking investors for their next projects.
  • Meet the producers in person and get to know the show in its early stages by attending table-reads and rehearsals.
  • Don’t set your expectations too high.

Would you consider investing in a Broadway show?

Photo: kevin dooley
BroadwayWorld, CNBC, New York Times

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This is a relatively long review of TurboTax 2012 Online, software for completing tax forms and submitting them to both the federal and state authorities. I’ve updated the review to reflect the changes to the software in 2012 (for filing 2011 tax returns).

Recently, the IRS began accepting federal tax returned filed electronically. Even before the IRS began accepting returns, you could still have completed your tax forms online through software. Programs like TurboTax, H&R Block, and Jackson Hewitt have been accepting customers and holding off on filing until now. This delay affected those who had itemized deductions, claimed the tuition and fees deduction, or claimed the sales tax deduction.

Many taxpayers are just getting started with their 2011 federal returns now. I’ve been using the services of an accountant for the past few years, and he was able to cut through the more confusing tax consequences of owning a business, saving me $15,000. Before my tax situation was complicated, however, I completed my taxes online using various software. Following a series of questions, completing and filing my 1040 form was easy.

Every year, the companies that provide tax e-filing services like TurboTax and H&R Block tweak their products, not only for the latest tax laws, but to improve features, making the process of tax filing easier. I took a look at TurboTax to see what changes the newest edition has to offer.

The first thing I noticed with TurboTax is the wide variety of products they have available. There is an option that is completely free for filing federal returns, but it is limited. This free version is for taxpayers whose returns can be completed using the 1040-EZ form, a simplified version of the 1040 form. If you have deductions, investments, a mortgage, or self-employment income, or if you want a step-by-step hand-holding guide to completing the forms, you will not be able to take advantage of the TurboTax Free Edition.

TurboTax offers several flavors in addition to the Free Edition, including Deluxe, Premier, Home & Business, and Business, each to handling more complicated tax situations above and beyond the lighter editions. The Deluxe Edition focuses on capturing all of your deductions. The Premier Edition does deductions, as well, but also includes the forms you need for investments like stocks, mutual funds, and rental properties. Home & Business covers all of the above as well as self-employment income, and the Business Edition is for anyone who is a partner in or owner of a corporation.

The editions are flexible; start with the Deluxe Edition, and as you come across features you need, TurboTax will ask if you’d like to upgrade — without charging you yet — to the edition that takes all of your needs into account. I started the Deluxe Edition to see how far I could go. I saw that for the most part none of the upgrades are needed if you are confident about your tax accounting abilities and are willing to enter your information directly into forms rather than have the software hold your hand through every decision.

Get your refund in as little as 8 days. E-file with TurboTax today. It’s Easy

Here is an overview of my entire process of completing my federal and state tax returns with TurboTax.

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401(k) Contribution Limits for 2012

by Flexo

Thanks to inflation, the maximum amount of money you may contribute to your 401(k) in 2012 will change. This applies to 403(b) accounts, as well. For 2009, 2010, and 2011, the maximum you may designate to your 401(k), not including your employer’s matching contributions, was $16,500, but in 2012, this will finally increase to $17,000. ... Continue reading this article…

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2012 Federal Income Tax Brackets and Marginal Rates

by Flexo

The IRS has finalized the 2012 federal income tax brackets, but most people aren’t concerned with these numbers until next year. In April 2012, you’ll need to be concerned with the 2011 tax brackets to file your 2011 income tax returns. Most taxpayers won’t need to deal with the 2012 rates until early 2013. While ... Continue reading this article…

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2011 Stimulus Package: American Jobs Act

by Flexo
Dollar - 2011 Stimulus Package

Update: The Buffett Rule, if implemented, could help pay for the American Jobs Act. As long as the public holds the general impression that economy isn’t favorable, and that’s certainly the case, for example, when unemployment is high or after a stock market crash, political leaders will propose stimulus plans to help move the country ... Continue reading this article…

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Goal Progress After April 2011

by Flexo

I last evaluated my progress towards my goals at the end of January, so it may be time to have another look. At the beginning of 2011, I set financial and personal goals for the year to keep me focused on improving not only my finances but other aspects of my self. Goal 1. I ... Continue reading this article…

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