This is fascinating - I'm actually looking at purchasing a property next year instead of continuing to lease. Would cost segregation work for a relatively small commercial property (around 5,000 sq ft)? And roughly what percentage of a building's value typically qualifies for accelerated depreciation?

Cost segregation absolutely works for smaller commercial properties, even at 5,000 sq ft. For education-focused buildings, typically 20-40% of the total value can qualify for accelerated depreciation depending on how specialized your setup is. Classrooms with built-in technology, specialized flooring, dedicated HVAC zones, and security systems often qualify. The study itself might cost $5,000-$8,000 for a property your size, but the tax savings usually exceed this cost in the first year alone. Consider working with a firm that guarantees their findings will produce savings exceeding their fee. Also, the study can be done years after purchase - you don't need to do it right when you buy the property.

Family employment is absolutely legitimate if done correctly. The key requirements: they must do real work appropriate for their age, be paid reasonable market wages for that work, have proper employment documentation (W-4, I-9, etc.), and actually receive the money (their own bank account). Keep detailed timesheets and job descriptions. For teenagers working in education, typical roles include administrative support, basic tutoring, materials preparation, social media management, and technology assistance. The tax advantage comes from shifting income to their lower tax bracket, plus the business deduction. They can even contribute to Roth IRAs with these earnings, creating incredible long-term tax advantages.

Thanks for clarifying! I'll definitely set up proper documentation systems including timesheets and job descriptions. They already have their own bank accounts, so that part's easy. Would it make sense to pay them as W-2 employees or as 1099 contractors? And I love the Roth IRA idea - never even thought about that benefit.

Did you find good quantitative sources for this? I'm interested in the topic but worried it might be too anecdotal without solid numbers to support the analysis.

Yes, there's excellent quantitative research available! The Brookings Institution has published several data-driven studies on stadium financing and economic impacts. There's also a comprehensive paper from the Federal Reserve Bank of St. Louis that analyzes dozens of stadium projects with detailed financial metrics. For your presentation, I'd recommend using the Congressional Research Service report that breaks down the tax subsidy costs at the federal level - it has great charts showing the effective taxpayer contribution to various stadiums built in the last 20 years. These sources provide plenty of hard numbers to support the policy analysis.

GILTI is interesting but might be too complex for a student presentation unless you're already familiar with international tax. QBI might be more accessible if you're not a tax specialist.

Thanks for this suggestion! Do you know roughly how much these payroll services cost annually? I've been doing everything manually and calculating taxes myself, but maybe it's worth paying for a service if it handles all these filings automatically.

I pay about $725 annually for HomeWork Solutions to handle everything for our nanny - which works out to around $60 per month. They handle all the tax calculations, provide direct deposit for my nanny, generate paystubs, and take care of all the quarterly and annual filings including W-2/W-3. The time and stress it saves me is absolutely worth the cost. They also have different service tiers depending on what you need. Some services like SurePayroll might be a bit less expensive, closer to $40-50 per month. Given the headaches and potential penalties of missing deadlines or calculating something incorrectly, I've found it to be money well spent.

Did you need the most expensive version of TurboTax for this feature? I used the Deluxe version this year and didn't see any option for filing W-2s for household employees.

That's a great point I hadn't considered! The initial setup being more labor-intensive makes sense. Did you find the professional help worth it compared to doing it yourself with software? And did they help you identify deductions you might have missed otherwise?

I definitely found professional help worth it, especially for that first year. My CPA found several deductions I would have missed, particularly around start-up expenses for the rental business and some travel costs related to property acquisition that I didn't know were partially deductible. After the first year, I've learned enough that I could probably use software, but I still prefer having a professional review everything. The peace of mind is worth it to me, especially since rental properties can trigger audits if certain deductions look unusual. Having someone who knows exactly what documentation to keep has been invaluable.

I used them last year for my rental and had a terrible experience. The first preparer clearly didn't understand passive activity loss limitations and made a huge error that would have cost me thousands. I had to request a different preparer and even then felt like I was explaining things to them rather than the other way around. If you go with H&R Block, make sure to specifically request someone who specializes in investment properties. The regular preparers mostly handle W2 and simple returns.

Thanks for sharing your experience. That's exactly what I was worried about - ending up with someone who mainly handles simple returns. I'll definitely ask specifically for an investment property specialist if I decide to go with them. Might be worth paying a bit more for someone with specific rental property experience instead.

That makes a lot of sense actually. He does still print out his emails and keeps them in folders! Do you think there's any actual advantage to paper filing these days?

Absolutely none! Electronic filing is actually more secure and has fewer errors than paper filing. The IRS even processes e-filed returns faster. The only "advantage" to paper is psychological comfort for people who grew up with it. Paper filing has about a 21% error rate compared to less than 1% for electronic filing. Plus with the IRS backlog, paper returns can take months longer to process. You're making the smart choice going digital!

This is really good advice. I once missed a retirement contribution code in box 12 and it messed up my Saver's Credit. How do you recommend double-checking these codes?