This is such a helpful thread! I'm dealing with a similar situation where I borrowed money from my uncle for a small business startup. We set up a formal loan agreement with 4% interest, and I've been making monthly payments including interest for about 8 months now. One question I haven't seen addressed - what happens if the total interest I pay him for the year ends up being less than $10? Do I still need to issue a 1099-INT, or is there actually a minimum threshold before it's required? I'm calculating that I'll probably pay around $180 in interest for the full year, so I'm definitely over the threshold, but I'm curious about the exact rules. Also, does anyone know if there are any special considerations when the loan is for business purposes versus personal use? I'm wondering if that changes anything about how I handle the 1099-INT or if it affects the deductibility on my end since this was for legitimate business expenses.

This thread has been incredibly helpful! I'm in a similar situation with my sister where I borrowed $15,000 for home repairs with a 3% interest rate. Reading through everyone's experiences, I'm now confident I need to issue a 1099-INT since I'll be paying well over the $10 threshold. One thing I wanted to add that might help others - if you're struggling with the paperwork like I was, your local VITA (Volunteer Income Tax Assistance) program often has volunteers who can help explain the 1099 process for free. I called my local site and they walked me through exactly which forms I needed and how to fill them out properly. They even helped me understand the timing requirements better than the IRS publications did. For anyone still confused about the process, don't hesitate to reach out to these free resources before spending money on services or making mistakes that could cause problems later. The VITA volunteers are IRS-certified and can give you the same accurate guidance without any cost.

The key thing to remember is documentation, documentation, documentation! I've been through an IRS audit on a similar mobile office setup and they want to see everything - photos of your workspace layout, a floor plan showing measurements, records of how you use each area, utility bills, maintenance receipts, etc. Also consider the depreciation method carefully. For a travel trailer used partially for business, you'll likely use MACRS depreciation over 7 years, but only for the business-use percentage. Keep detailed records of any improvements or repairs too - some might be immediately deductible while others need to be depreciated. One more tip: if you're truly using this as your primary business location, make sure your business address reflects this on all your tax forms and business registrations. Consistency across all documents will help if you ever face questions from the IRS.

One thing I haven't seen mentioned yet is the potential impact on your ability to claim vehicle expenses if you're using the trailer as your primary office. Since the IRS generally doesn't allow you to deduct commuting expenses to your regular place of business, if your trailer IS your office, you might lose the ability to deduct mileage for local business trips that start and end at your trailer location. However, if you travel to client meetings or other business locations FROM your trailer office, those miles should still be deductible. Just make sure you're tracking everything carefully - keep a detailed mileage log with dates, destinations, business purposes, and odometer readings. Also, consider getting a separate business phone line and internet connection if possible. Having dedicated business utilities makes it much easier to justify and document the business use percentage of your trailer expenses.

Something nobody's mentioned yet is that if you make under $73,000, you can use the IRS Free File program to access premium tax software for FREE. The software companies hide this option but are required to offer it. Go through the IRS website directly (https://www.irs.gov/filing/free-file-do-your-federal-taxes-for-free) instead of the tax software sites. I used to pay $89 for TurboTax Deluxe plus $49 for state filing, but now I get the exact same software completely free through this program. The income limit increases slightly each year too.

I switched from TurboTax to FreeTaxUSA two years ago and haven't looked back. The interface took a little getting used to at first, but it handles everything I need including my rental property income and business expenses. What really sold me was the price - I went from paying around $150 total (federal + state) with TurboTax to about $25 with FreeTaxUSA. One thing I'd recommend is starting your return early with whatever software you choose so you have time to compare. Most platforms let you input all your info and see the results before you actually pay and file. That way you can test drive a few options and see which interface you prefer and if the refund amounts are comparable. For your side business, make sure whichever software you pick has good guidance on Schedule C deductions. That's where you can really save money if you're tracking business expenses properly - things like mileage, supplies, equipment, even a portion of your phone bill if you use it for business.

I'm so confused by all this HSA stuff 😫 I made a contribution in Feb this year but totally forgot to tell my HSA bank it was for last year. Can I still somehow count it for 2024 taxes or am I screwed?

Just wanted to add another important point that helped me - if you're making a prior year HSA contribution, double-check your HSA eligibility for the ENTIRE prior tax year before contributing. I almost made a costly mistake last year when I realized I had overlapping coverage with my spouse's FSA for two months, which made me ineligible for HSA contributions during that period. The IRS is pretty strict about this - if you weren't HSA-eligible for even part of the year due to other health coverage, disqualifying insurance, or Medicare enrollment, it can affect how much you're allowed to contribute. The "last month rule" can sometimes help, but there are testing period requirements too. I ended up using the IRS Interactive Tax Assistant tool on their website to verify my eligibility before making the contribution. It's free and walks you through all the eligibility requirements step by step. Better to check now than deal with excess contribution penalties later!

Just to add one thing no one mentioned yet - if the buyer pays you more than $600 in interest during the tax year, you should technically issue them a Form 1098 showing the mortgage interest they paid you. This allows them to potentially claim the mortgage interest deduction on their taxes. I use a simple spreadsheet to track my owner-financed property payments. I have columns for payment amount, interest portion, principal portion, and remaining balance. Makes tax time so much easier!

Great advice in this thread! One additional consideration for @ApolloJackson - since you mentioned this was your primary residence before becoming a rental, make sure you understand the depreciation recapture rules. If you claimed depreciation deductions during those 2 years when it was a rental property, you'll need to "recapture" that depreciation and pay taxes on it at a rate up to 25% (rather than capital gains rates). This recapture happens regardless of whether you use installment sale treatment - it's required to be recognized in the year of sale. Only the capital gain portion above the depreciation recapture can be spread out over the installment payments. Your CPA will be able to calculate this for you, but it's something to factor into your tax planning since it could affect your 2025 tax liability even though you're receiving payments over 15 years. Also, keep excellent records of all maintenance, improvements, and expenses related to the property during your ownership - these can help reduce your overall taxable gain!