Paying Someone to do Your Taxes Is Like Paying Someone For Sex...

... I'm only going to do it if I'm truly desperate*.

There aren't too many hacks for the regular person doing taxes. As byzantine as our tax code is, at the heart of it is a relatively simple system to prevent people from robbing the government blind (at least the average dude/tte with a 9-5). Fact of the matter is, there's not a ton of awesome stuff you can do to lessen your tax burden. On the other hand, there is one thing you can do to save money this season: Do your own damn taxes.

Even though we're not married, I do both our tax returns, partly because I'm worried Susan will fuck it up and partly because Susan prefers me to do it. 

Here is a snapshot of our tax situation:

- My income comes from W2s, writing residuals, and investment income (both interest and dividends). 
- I itemize my deductions, which include business expenses, mortgage interest, property tax and charitable contributions.
- I have moving expenses from the previous year and will split income over two states for the coming year.
- Susan is self-employed and works at no less than 6 hospitals who pay her in a variety of 1099s and W2s. This year she'll work at close to a dozen hospitals in two different states and will have moving expenses in addition to normal business expenses.
- Susan also has a second job from which she derives income (ballet dancer), with a completely different set of deductions.  
- Both of us have IRA contributions that require us to track our cost basis. In addition, Susan has a solo 401K which I administer. 

To further complicate things, I know little about taxes and have little-to-no training. I don't even think I started doing taxes until I left school and got my first big boy job.

Sounds like a nightmare right? 

Eh - not so much. 

In this day and age, I don't understand how there are people out there who don't just use Turbotax or the H&R Block equivalent. I use Turbotax even though I think I could just fill out the forms because it's convenient. All my previous returns and info is stored in one place. It's easier to e-file the return. They're on tax law changes like a hound on a pork chop. Plus, the software is really, really good because making easy-to-use tax software is literally the only thing they do. Plus, the best feature is the real-time tracking of your debt/refund for both federal and state. This has saved us thousands of dollars by allowing us to plan activities that are deductible and, just as importantly, educating me on which deductions aren't.

For example: Susan makes too much for her student loan interest to be deductible. However, I discovered that she could make Solo 401k contributions as a self-employed individual that would drop her income low enough for the student loan deduction to take effect. Only because I saw her tax liability drop when I toyed with the numbers was I aware that this was possible.  

With Turbotax Federal costing $35, there really doesn't seem to be any advantage in paying a pro (again, for the average non-business owner). I've read that the average tax outfit charges 300 bucks to do a regular person's taxes. That's not a CPA, who's at least going to give some peace of mind that a competent person is in charge. $300 gets you a seasonal worker bee. They come in during January, take a quick course where they're trained to ask the same questions the software would and then are released into the world. You're paying for the expensive illusion of security as they ask you questions and punch in the numbers for you. It takes longer. Information can get lost or miscommunicated. They can move a decimal point and not notice because this is their fourteenth return of the day. All for a nine hundred percent markup. 

Final note: Turbotax has started to add a whole bunch of BS add-ons to their suite. Basically everything except the core product is a rip-off. You can safely skip their audit defender option, for example (your odds of being audited are so incredibly low). Here's another subtle rip-off that's avoidable - Turbotax reels you in with a low-cost Federal Version and then gouges you for the state version. In Illinois, that's an extra 40 bones. But here's the thing: Illinois uses the federal filing numbers as a starting point for state taxes. Once I learned this, I would file federal taxes through Turbotax and then delete the state forms. Then I would simply download a copy of my federal forms from Turbotax (free and instantly) and then input the numbers into the Illinois State Tax Portal. This year it took me about 15 minutes, working out to an hourly savings rate of $160. Screw paying extra.

For the record, Turbotax is a deductible tax-preparation expense. It's just a smaller one than you would pay a preparer.  

*I also feel this way when it comes to paying for parking. Living in Chicago was... difficult in this regard.