We're in our late 30's and my Mom does our taxes for us. She's an accountant. My wife's part of the taxes are pretty straightforward, but mine are pretty complicated. There's an awful lot of gray area in the way the tax laws are written. What they read as to a normal English speaking human being is not what they actually mean. Without having someone that's up to speed on all the latest rulings, I'd be hosed.
If your taxes are complicated I don't mean to pick on you... my roommates must have it simple.
We're all renters, they have no investments, they might have student loan interest, and one of them has had multiple jobs within the past year. One or both do tutoring on the side, but since I doubt they track business expenses and mileage that's still pretty simple to report as business income with no expenses. And if they did that themselves it might incentivize them to start tracking those things. One of them is a teacher so there's up to a $250 above-the-line deduction available for educator expenses, but the hardest part of taking that is keeping track of the receipts; all that's left is knowing the limit and sticking the number in the form.
I've been doing my taxes ever since I first had reportable income with a summer job in high school; my Dad showed me how to do it. He would tell me how complicated his taxes were with being married, deductions, and the AMT, so I theorized that if I kept up with doing taxes myself year to year, I'd gradually learn how to handle the complexities a handful at a time. So far it's worked, and if last year were the first time I'd ever done taxes myself, I'd be completely lost! (majority freelance income, SEP contributions, estimated taxes, self employed health insurance deduction, HSA, capital losses, dividends, foreign tax credit, ...)
