I used to be a coder for TuboTax some time ago. To this day they're still limited in a few areas, schedule C has many, many sub-sub schedules that can come into play and they do not account for them well. It's not just TT either, it's every company, they only code to the most common denominator of needs out there.I've been doing my own taxes since about 2001 / 2002 and including since 2008 when I've been a 1099 self-employed contractor through to present day. I've used both TurboTax for self-employed folks, as well as H&R Block. It doesn't really take digging and digging in tax codes when you do those as they walk you through everything, won't allow you to do certain things based on your answers to other questions, etc. They sorta guide you along.
I've learned that for as much as you can legit write off as business expenses, your taxes owed don't really come down that much. I'm talking peanuts. Now, I'm not exactly donating or buying tens of THOUSANDS of dollars of things like the Trackholes do - so they may see a bigger dent in what they owe - but if they try and write off TOO much stuff vs. how much they raked in "income-wise," then surely red flags would go up... and the more money you make, the more likely you are to get a possible audit.
(of course, I don't remember if Tim ever mentioned using programs like that or if he just dumps all their receipts off at an accountant to let him / her handle the work)
The software is only as good as the specs it was written from, the specs are created by the company morphing ever-changing tax codes into functional documents and then the process to keep up. It's a total game and not one to put your faith in if you do a lot of investments, own property for rentals or have a complicated business structure. Always double check everything.
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