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Picked the cheap tax software over a CPA this year and got audited in April.
I figured hey, how bad could TurboTax be for a simple W-2 and some freelance income? $79 felt way better than the $400 my usual guy wanted. Stupid me didn't catch that I fat-fingered a number in my mileage deduction by about 2,000 miles. The letter from the IRS came on a Tuesday, and I had to spend 6 hours digging through bank statements to prove I actually drove for those gigs. My CPA laughed when I called him, said "shoulda called in January." Now I'm out $150 for the software plus his fee to fix it. Is there any scenario where DIY tax prep actually works out for people with side hustles?
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betty1264mo ago
Oh I learned that lesson with a rental property once, what a mess.
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foster.ruby4mo ago
Yeah @betty126 know that feeling all too well. But here's something most people don't think about - insurance companies can drop you like a hot potato if you file too many claims on a rental property, even small ones. They'll just refuse to renew your policy and then you're stuck paying double somewhere else. Had a friend who learned that the hard way after a couple of plumbing claims and now she can barely get anyone to cover her place. That's the hidden cost people don't talk about when they say "just file a claim.
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