As someone who actually owns a legitimate small business that struggled to get PPP funds while following all the rules, I have zero sympathy. Your cousin committed FRAUD against taxpayers during a national emergency. People like him are why so many legitimate businesses couldn't get funded quickly enough.

I understand you're worried about your cousin, but this is unfortunately a very serious federal crime. Creating a fake Schedule C to obtain $26K in PPP funds is textbook fraud, and the fact that he didn't file taxes for 2020-2021 will make this case extremely easy for investigators to identify and prosecute. The government has specifically allocated resources to investigate PPP fraud cases of all sizes, not just the large ones. They're using automated systems to cross-reference loan applications with tax filings, so missing returns paired with a Schedule C-based loan application will absolutely trigger a review. Your cousin needs to understand that simply paying back the loan doesn't eliminate criminal liability - the crime was committed when he submitted false information to obtain the funds. He should immediately consult with a criminal defense attorney who specializes in federal financial crimes (not just a tax attorney) to discuss his options, which may include voluntary disclosure and cooperation. The statute of limitations for PPP fraud has been extended to 10 years, so time is not on his side. The sooner he addresses this proactively with proper legal counsel, the better his chances of minimizing the consequences.

One more thing to consider - if the towing was for a vehicle that was abandoned on your property (like an old tenant left a car behind), that might fall under different rules than if it was just for parking enforcement. Different circumstances can change how you categorize the expense. Just something to keep in mind!

As someone who's been dealing with rental property taxes for several years, I wanted to chime in on the Safe Harbor vs. regular deduction question. The confusion is totally understandable! Safe Harbor rules are really specific - they're meant for routine maintenance items that you can elect to deduct immediately rather than capitalize. Think things like repainting, fixing leaky faucets, or replacing broken windows with similar quality items. Your towing situation is definitely deductible, but it falls outside the Safe Harbor provisions because it's more of an operational/management expense. It would go under "Other expenses" or "Legal and other professional fees" on Schedule E, depending on how your tax preparer categorizes property management costs. The good news is that it doesn't matter for your bottom line - you still get the full deduction for your portion of the cost. Just keep that receipt and a brief note about why it was necessary for your rental business!

Another option to consider - while you can't deduct your time/services, you could potentially partner with the non-profit and become a sponsor instead. I'm a DJ and I "sponsor" events with my services, then the organization gives me advertising/recognition as a sponsor. This way I get business exposure/marketing (which IS deductible as a business expense) in exchange for my services. Talk to your tax professional, but this arrangement might work better for you than trying to claim a charitable deduction. The key is making sure there's legitimate marketing/advertising value to your business.

People are giving good advice about what you can't deduct, but let me offer you another approach. instead of donating your time, you could offer to do the event at your normal fee and then donate back a portion of what you earn. This way you: 1) Get paid (yay income!) 2) Can take a legitimate deduction for your cash donation 3) Build your professional reputation instead of being seen as "free" You pay taxes on the income but get the deduction for the donation. And most importantly, you maintain the perceived value of your services while still supporting causes you care about.

Bit of a tangent, but what gambling log app do people recommend? I've been using a paper notebook which is getting unwieldy. Is there a good mobile app that lets you log sessions and wins/losses on the go?

This is exactly why I always recommend keeping contemporaneous notes while gambling! The key thing to remember is that your gambling log should reflect the actual time you were gambling, not when the casino's "gaming day" officially ends. Here's what I do: I note the actual calendar date and time when I start and stop gambling, regardless of what the casino considers their "gaming day." If I'm playing at 2am on February 15th, that's what goes in my log as February 15th activity. When I get a W-2G that shows February 14th for that same jackpot, I make a note in my log like "W-2G dated 2/14 due to casino gaming day policy" next to the February 15th entry. This creates a clear audit trail. The IRS has been pretty consistent that they want to see gambling activity tracked by actual calendar days, not casino accounting periods. Your approach of wanting to stay organized by calendar days is correct - just make sure you have those reconciliation notes to explain any date discrepancies on your tax forms.

Quick tip for the original poster: For the FUTA Employer paid YTD field in QuickBooks, make sure you're only entering what you've actually paid to the IRS so far this year, not what you've accrued. If your FUTA liability is less than $500 per quarter, you might not have made any payments yet this year (since you'd pay it all with your annual 940 form). In that case, the YTD amount would be zero until you make that annual payment.

Found this explanation on the IRS website that might help with understanding FUTA vs other employer taxes: https://www.irs.gov/businesses/small-businesses-self-employed/understanding-employment-taxes Big difference with FUTA is it's ONLY paid by employers (not split with employees like Social Security/Medicare) and it's only on the first $7k of wages per employee. Easy to mix up with other payroll taxes!