Does Cash App Taxes handle self-employment income well? I have a small side business and have been using TurboTax Self-Employed, but it's so expensive.

Yes, Cash App Taxes handles self-employment income quite well for straightforward situations. It has all the Schedule C forms and walks you through business deductions, home office calculations, and quarterly estimated payments. Where it might fall short is if you have very complex business situations like inventory management, multiple businesses, or specialized industry deductions. For a side gig bringing in $4k like the original poster mentioned, it would be perfectly fine. I have a photography side business that makes about $12k annually and it works great for me.

Do you think a CPA is worth it for simpler returns? I just have a W-2 job and a mortgage, no complicated stuff.

I used a CPA last year and she missed a huge education credit I was eligible for. When I pointed it out she acted like I was being difficult. Going back to doing it myself this year.

16 Do you use a specific software for keeping separate books for multiple LLCs? I've been using QuickBooks but it gets expensive with multiple companies.

7 I use Stessa for my rental properties - it's specifically designed for real estate and allows you to track multiple properties and entities. It's much more affordable than having separate QuickBooks accounts for each LLC. For non-real estate businesses, I've heard good things about Xero which has better multi-entity functionality at a lower price point than QuickBooks. The key is making sure you have clean, separate financial statements for each LLC that clearly show income, expenses, assets and liabilities, regardless of which software you use.

1 That's a really good point! Does anyone know about Texas requirements for multiple LLCs? We're paying the franchise tax for our parent LLC, but I'm not sure if we need to file anything for the property LLCs too.

11 Great point! I actually messed this up last year. Spent hours tracking investment interest and other itemized deductions only to have my tax software automatically take the standard deduction because it was higher. Felt like such a waste of time.

5 Excellent reminder! To add a bit more detail - even if you can't benefit from the deduction this year because you're taking the standard deduction, you should still complete Form 4952 to establish your carryforward amount for future years when you might itemize. Also worth noting that if you're in a high-tax state like California, New York, or New Jersey, you're more likely to benefit from itemizing since state and local tax payments (though capped at $10,000) plus your margin interest might push you over the standard deduction threshold.

2 Is there a specific way to document this? My brokerage account is kind of a mess with deposits, withdrawals, and margin usage all mixed together throughout the year.

Do these free tax prep services handle back taxes from previous years? I thought they only did current year returns during tax season.

You're right that many VITA and TCE sites focus primarily on current year returns during the regular tax season. However, some locations do offer assistance with prior year returns, though this varies by site. You'd need to call specific locations to ask about their services for back tax returns. If free services aren't available for prior years in your area, consider a low-cost tax professional instead of the major chains - often local enrolled agents or CPAs will handle back taxes for much less than the big tax preparation companies, especially for straightforward returns.

I got one of those last year. It's scary but doesn't mean they're immediately coming for your stuff. You usually have 30 days to respond, and if you call them and show you're trying to fix the situation by filing and setting up payments, they'll often put a hold on collection activities.

Just be careful with this approach. The IRS looks closely at family businesses that suddenly put family members on payroll, especially kids in college who aren't clearly providing services. Make sure you have solid documentation showing actual work being performed, regular payments (not just lump sums), and pay that's comparable to what you'd pay a non-family member.

This is extremely helpful! We're paying about $42,000 per year for her tuition and housing. If we pay the school directly, that wouldn't count toward the gift tax limits at all? And we could still give her additional money up to the $36,000 combined annual exclusion for living expenses?

Exactly! Direct payments to educational institutions for tuition are completely exempt from gift tax. However, note that only tuition qualifies - not room and board, books, etc. Those would still fall under your annual gift exclusion. So yes, you could pay her tuition directly to the school (let's say $30,000) with no gift tax implications, PLUS give her up to $36,000 ($18k from each parent) for other expenses. That's a total of $66,000 you could transfer for her benefit without any gift tax reporting requirements.