This is such valuable information! I've been struggling with this exact issue as a freelance consultant. One thing I'd add is to be extra careful about the "temporary vs. indefinite" assignment rule. If you're working at the same out-of-town location for more than a year, the IRS might consider it a regular workplace rather than temporary travel, which could affect your mileage deductions. I learned this the hard way when I had a 14-month contract at a client site. The IRS questioned whether my travel there was truly "temporary" business travel. Fortunately, I had good documentation showing the contract was originally for 6 months and got extended multiple times, which helped prove it started as temporary work. Also, don't forget to track your mileage to and from airports if you're flying to business destinations! That local travel is deductible too and can add up over the year.

As someone who works from home and does frequent client visits, I want to emphasize how important it is to establish your home office properly with the IRS. Make sure you're actually using the home office deduction (Form 8829) if you qualify - this solidifies your home as your tax home and makes all those business trips clearly deductible. One mistake I see people make is being inconsistent about their "regular workplace." If you sometimes work from coffee shops, co-working spaces, or client offices regularly, it can muddy the waters about where your actual tax home is located. The cleaner you can make the case that your home office is your primary workplace, the stronger your mileage deduction claims will be. Also keep in mind that if you use the simplified home office deduction method, you can still claim all your business mileage - the two deductions work together, not against each other. I've seen people worry unnecessarily that taking the simplified home office deduction would somehow limit their mileage claims.

I'm a landlord and I always tell my tenants to just write checks to each other for their portion, then one person pays me the full amount. No digital trail, no 1099-K headaches. Old school but effective!

As someone who works in tax preparation, I can confirm that personal transfers between roommates for shared expenses like rent are not considered taxable income. The 1099-K reporting threshold is meant to catch unreported business income, not legitimate cost-sharing arrangements. However, I'd recommend keeping good documentation just in case. Save your lease agreement, rent receipts to your landlord, and a simple log showing the connection between your roommate transfers and actual rent payments. This creates a clear paper trail showing these are reimbursements, not income. The check suggestion from Mae is actually really smart - it completely sidesteps the digital reporting requirements while still being traceable if needed. Plus many banks now let you deposit checks by taking a photo, so it's not as inconvenient as it used to be. Don't stress too much about this. The IRS is primarily looking for people who receive significant payments for goods/services and don't report that income. Your rent-splitting arrangement is clearly documented and legitimate.

I'm dealing with a very similar situation and this thread has been incredibly helpful! I've been playing on Underdog and PrizePicks for about 6 months and have around $2,400 in net winnings, but like many others here, I had no clue about the tax implications until now. After reading through all the advice, I immediately went and downloaded my transaction histories from both platforms. Found them exactly where people mentioned - under Account Settings for PrizePicks and buried under Account > History for Underdog. The CSV exports are actually pretty detailed and show everything I need. One thing I noticed that might help others - both platforms also show your "net deposits" vs "net withdrawals" in their account summaries, which gives you a quick sanity check on whether you're actually up or down for the year before diving into the detailed transaction logs. I'm definitely going to start that Google Sheets tracking system going forward and set up automatic transfers to a separate tax account. Based on the 25-30% rule mentioned throughout this thread, I should be setting aside about $600-720 for taxes on my current winnings. Thanks especially to everyone who shared specific details about finding the transaction histories and explained the itemized vs standard deduction decision. This community knowledge is way more practical than anything I could find through official IRS resources!

This thread has been incredibly valuable! I'm in a similar boat with about $4,100 in winnings from Underdog and PrizePicks over the past year, and I was completely lost on how to handle the tax side of things. After reading through everyone's experiences, I've already downloaded my transaction histories from both platforms (thanks for the specific navigation tips - would have never found them otherwise!). The CSV exports are way more detailed than I expected and actually make the whole process seem manageable. One question I haven't seen addressed yet - does anyone know if there are any differences in how the IRS treats player props vs traditional DFS lineups? I've been doing mostly player props on these platforms rather than full lineup contests, and I'm wondering if that affects the tax classification at all. Also planning to implement that Google Sheets tracking system starting immediately. The idea of setting aside 30% of each withdrawal automatically is brilliant - I wish I had thought of that earlier in the year. Better late than never though! Really appreciate everyone sharing their real-world experiences here. This kind of practical advice is exactly what us casual players need but can never find in official tax guidance.

Just wanted to share another perspective on this - I made the same mistake when I first started my business thinking I could deduct gift card purchases immediately. The IRS audited me two years later and made it very clear that gift cards are treated like cash advances, not business expenses until actually used. What saved me was keeping meticulous records of exactly what I purchased with each gift card and when. I had a simple spreadsheet with columns for: gift card purchase date, amount, vendor, actual use date, what was purchased, and business purpose. This made it easy to match up the gift card purchases with the legitimate business expenses when they actually occurred. One tip that helped me - when you do use the gift cards, take photos of both the gift card transaction AND the items you're purchasing. This creates a clear paper trail showing the business purpose of each expense. My accountant said this level of documentation is exactly what you need if the IRS ever has questions about your deductions.

Great advice from everyone here! As someone who went through a similar situation with my first business credit card bonus, I want to emphasize one thing that really helped me: create a dedicated folder (physical or digital) specifically for gift card documentation. When I bought gift cards, I immediately scanned the receipt and noted the date, amount, and intended business use. Then when I actually used each card, I'd scan that receipt too and file it in the same folder with a note linking it back to the original gift card purchase. This made tax prep SO much easier because everything was connected. Also, don't forget that some business credit cards actually code certain gift card purchases differently than others. My Chase Ink card didn't give me points for Visa/Mastercard gift cards, but it did for store-specific ones like Home Depot or Amazon. Just something to keep in mind if you're trying to maximize both the signup bonus and ongoing rewards! One last tip - if you're buying a lot of gift cards at once, consider spreading the purchases across a few days rather than doing it all in one transaction. It looks more natural from a bookkeeping perspective and avoids any potential red flags if you ever get audited.

Has your husband asked his school about emergency loans or payment plans? Many law schools have emergency funds or can defer some costs that might reduce how much you need to pull from retirement. Also look into Grad PLUS loans which can cover living expenses, not just tuition. Might be better long-term than raiding retirement.

Just want to emphasize what others have said about the Traditional IRA rollover approach - this is likely your best bet. When your husband leaves his job, he can roll the 401k into a Traditional IRA, then withdraw for qualified higher education expenses (tuition, fees, books, supplies) without the 10% penalty, though you'll still owe income tax. One important detail: make sure to keep detailed records of all education expenses you're using the withdrawal for. The IRS can ask for documentation, and you want receipts showing the expenses were for qualified items. Room and board don't qualify for the education exception, but tuition and required books/supplies do. For the medical debt portion, if your unreimbursed medical expenses exceed 7.5% of your adjusted gross income, that portion can also avoid the 10% penalty. You'll need good documentation for this too. The timing works in your favor since he's starting school soon - you can coordinate the withdrawal timing with when you actually incur the education expenses.