One thing I'd add that hasn't been mentioned yet - if you're going to claim therapy expenses as medical deductions, make sure your therapist is properly licensed. The IRS requires that mental health services be provided by a licensed professional for them to qualify as deductible medical expenses. Also, keep in mind that if your employer offers an Employee Assistance Program (EAP) that covers some therapy sessions, you should subtract any benefits you received from your total out-of-pocket costs when calculating your deduction. Only the amount you actually paid out of pocket can be deducted. Given that you spent $19K, it's definitely worth exploring all these options! That's a substantial amount that could potentially provide significant tax relief if you can meet the AGI threshold for itemizing.

This is such helpful information! As someone who also spent a significant amount on therapy last year (around $12K), I really appreciate seeing all the different perspectives and resources shared here. One additional consideration I'd mention is timing - if you're planning to claim therapy expenses for this tax year, it might be worth front-loading some of your 2025 therapy payments into late 2024 if that helps you cross the 7.5% AGI threshold for medical deductions. You can prepay for sessions or pay outstanding balances before December 31st and still claim them for the current tax year. Also, don't forget that travel expenses to and from therapy appointments can also count as deductible medical expenses! If you're driving a significant distance to see your therapist, you can deduct either the actual costs (gas, parking) or use the standard medical mileage rate, which is 22 cents per mile for 2024. Every bit helps when you're trying to reach that threshold. Thanks to everyone who shared their experiences with the various tax services and tools - definitely going to look into some of these options myself!

Missed tax filings happen! I screwed this up when starting my S Corp too. Be sure to file that zero return ASAP. Quick tip - get a tax calendar app or set quarterly reminders so this doesn't happen again. The IRS has very specific due dates for S Corps that are easy to miss.

Don't panic - this is actually a pretty common mistake for new S Corp owners! Here's what you need to do: 1. **File the missing Q1 Form 941 immediately** - Yes, you needed to file even with zero wages. File it as a "zero return" showing no wages, no taxes withheld, etc. There may be a small penalty, but it's usually minimal for first-time filers. 2. **For your current quarter** - Since you haven't paid yourself yet, you technically don't have payroll to report. But here's the important part: as an S Corp owner providing services, you need to start taking a reasonable salary soon. The IRS doesn't like when S Corp owners avoid payroll taxes by only taking distributions. 3. **Going forward** - Set up quarterly reminders for Form 941 filings (due dates are April 30, July 31, October 31, and January 31). Even if you have zero payroll activity, you still need to file. The good news is that since this is your first offense and the amounts are relatively small, penalties should be manageable. Focus on getting compliant now rather than worrying about what's already happened. You've got this!

I've been dealing with similar raw land investment tax questions and wanted to share what I learned from my CPA who specializes in real estate investments. The improvements you mentioned (gate, road grading, electrical) are definitely capital improvements that get added to your cost basis rather than deducted currently. This is actually beneficial long-term because they'll reduce your capital gains when you sell. One thing I don't see mentioned yet - make sure you're tracking which improvements are considered "land improvements" versus potential "building improvements" for future depreciation purposes. When you eventually develop the property, some of these costs (like the electrical infrastructure) might qualify for faster depreciation schedules than others. Also, double-check that you're not missing any deductible expenses you ARE entitled to now: property taxes, loan interest if you financed any of this work, professional fees for surveys or legal work, and any legitimate ongoing maintenance costs. These add up and can provide some current tax relief while you wait to benefit from the capitalized improvements. Keep every receipt and document the business purpose of each expense. The IRS is pretty strict about raw land deductions, so good documentation is your best protection.

I'm dealing with a very similar situation with my raw land investment, and after going through this whole process last tax season, I wanted to share what I learned that might help you avoid some mistakes I made. First, you're absolutely right to be thinking about this now - documentation is everything with raw land improvements. The IRS is particularly strict about these deductions because so many people try to inappropriately deduct capital improvements as current expenses. Your gate, road work, and electrical installation are definitely capital improvements that must be added to your cost basis. However, don't overlook the expenses you CAN deduct currently: property taxes you've paid, interest on any loans used for the purchase or improvements, and professional fees (surveys, legal, etc.). One thing I wish I'd known earlier - start tracking whether your improvements are "land improvements" versus potential "depreciable assets" for when you eventually develop. Your underground electrical work, depending on how it's installed, might have components that qualify for depreciation once you build and place rental property in service. Also consider whether you want to explore any income-generating activities on the property (like the hunting leases someone mentioned) that could change your tax treatment. Even small amounts of income can sometimes shift how the IRS views your property from pure investment to income-producing. Keep every receipt, take photos, and document the business purpose of each expense. When you eventually sell or develop, this preparation will save you thousands in taxes and potential audit headaches.

One more thing to consider - check if your area has any rural development grants or infrastructure improvement programs available. Many counties and states offer cost-sharing programs for rural road improvements, especially if multiple property owners participate. I found out about a USDA Rural Development grant that covered 40% of our road improvement costs when we went through a similar situation. We had to form a small road association with our neighbors and apply as a group, but it saved us thousands. The application process took about 6 months, but it was worth the wait. Also, some utility companies will contribute to road improvements if they need better access for maintenance - worth asking your electric, gas, or phone companies if they'd be interested in cost-sharing since better road access benefits their service capabilities too.

Great question about rural road improvements! I've dealt with similar situations professionally, and there are definitely some key steps to follow. First priority is determining road ownership through your county recorder's office - this is absolutely critical before spending any money. Many rural roads exist in legal gray areas where ownership isn't clearly defined, which can create huge problems later. For tax implications, if you own the road section, the paving cost gets added to your property's tax basis (helpful when you sell), but won't give you an immediate deduction. However, there's one exception many people miss - if you use part of your property for business purposes (home office, rental, etc.), a portion of road improvements might qualify as a business expense. You'd need to work with a tax professional to calculate the business-use percentage. Also consider getting multiple quotes - $15,000 for 1/4 mile seems reasonable for basic asphalt, but prices vary wildly based on access, prep work needed, and local contractors. Some areas offer chip seal as a middle ground between gravel and full asphalt that costs about 40% less. Finally, document everything meticulously if you proceed - photos, contracts, receipts, property surveys. This documentation will be essential for tax basis calculations and potential future property disputes.

As someone who's navigated S-corp structures for irregular income streams, I can share some insights on the payroll timing question. You don't need to match salary payments exactly to when endorsement money comes in, but you do need to maintain regular payroll intervals - typically monthly or bi-weekly works best for single-person S-corps. What I've found effective is setting up a consistent monthly salary payment based on projected annual earnings, then adjusting at year-end if needed. This keeps the IRS happy with regular W-2 wages while managing cash flow. Just make sure you have enough cash reserves to cover the salary payments during slower income periods. For payroll services, I'd actually recommend starting with something simpler than ADP for a single-person operation. Services like Gusto or QuickBooks Payroll are much more cost-effective (usually $40-80/month vs $150+ for the big providers) and handle all the federal/state compliance requirements just as well. You can always upgrade to a more robust solution if the business grows significantly. One often-overlooked tip: consider setting up a separate business checking account specifically for payroll to keep things clean and make year-end accounting much easier. The additional bank fees are usually minimal but the organizational benefits are huge come tax time.

Just wanted to add a perspective from someone who's been through this transition recently. I set up an S-corp for my photography business last year after hitting similar income levels, and one thing that caught me off guard was the quarterly estimated tax situation. Even with payroll withholding on the salary portion, I still owed a significant amount at year-end because the distributions weren't being withheld for taxes. Make sure your roommate either increases his withholding rate on the salary portion to cover the tax liability on distributions, or gets into a disciplined quarterly estimated payment routine. Also, since NIL income can be pretty volatile, I'd suggest he keeps detailed monthly P&L records. Not just for tax purposes, but it really helps when projecting reasonable salary amounts for the following year. The IRS likes to see that your compensation decisions are based on actual business performance data rather than just tax minimization strategies. One last tip - if he's working with multiple sponsors/brands, consider having separate contracts flow through the S-corp rather than mixing personal and business relationships. It makes everything much cleaner from an accounting perspective and strengthens the legitimate business purpose of the entity.