Great question about tax-loss harvesting for UTMAs! One important consideration that hasn't been mentioned yet is the impact on financial aid eligibility. UTMA assets are counted as student assets on the FAFSA at a much higher rate (20%) compared to parent assets (5.64%). While harvesting gains to step up basis is tax-smart, you might also want to consider the timing of when to do this relative to college planning. If your kids are getting close to college age, you may want to weigh the tax benefits against the potential impact on financial aid calculations. Also, make sure you're keeping detailed records of all these transactions. When your children eventually take control of the accounts, having clear documentation of cost basis adjustments will be crucial for their future tax planning.

This is excellent advice about the FAFSA implications! I hadn't considered how the 20% assessment rate on student assets could impact financial aid eligibility. This creates an interesting trade-off between tax optimization and college funding strategy. For families with younger children, the gain harvesting strategy makes perfect sense since you have years to benefit from the stepped-up basis. But as you get closer to college years, it might be worth running the numbers to see if the tax savings outweigh the potential reduction in financial aid. Another timing consideration: if you're planning to gift additional funds to the UTMA accounts, it might make sense to harvest gains first to free up "room" under the $1,250 threshold before adding new money that could generate additional dividends or interest. The record-keeping point is crucial too. I'd recommend creating a simple spreadsheet tracking each sale/repurchase transaction, the gain realized, and the new cost basis. Your kids will thank you for this documentation when they're older!

I had the same issue last year - took almost 3 weeks for mine to show up. The mail system seems really slow with these verification letters. If you're getting anxious about it, definitely call that number Aisha mentioned. Also worth double-checking that your mailing address on file with the IRS matches exactly where you want it sent. Even small differences like "St" vs "Street" can cause delays. Hang in there!

Had to deal with this exact situation a few months ago - the PIN took about 12 business days to arrive for me. One thing that helped speed up the process was making sure I had informed delivery set up through USPS so I could track when mail was coming. Also, when you do call that 800 number, have your SSN and the reference number from your original verification letter ready - it'll save you time on hold. The whole process is frustrating but you're definitely not alone in this!

Don't forget about making quarterly estimated tax payments! This was my biggest shock as a new 1099 contractor. If you wait until the end of the year to pay all your taxes, you might get hit with underpayment penalties. The due dates are April 15, June 15, September 15, and January 15 (for the previous year). You can pay online through the IRS Direct Pay system. I learned this the hard way and had to pay an extra $425 in penalties my first year.

As someone who just finished their second year as a 1099 contractor, I wish someone had told me about the home office deduction earlier! If you use part of your home exclusively for work, you can deduct either a portion of your home expenses (utilities, rent/mortgage interest, etc.) or use the simplified method which is $5 per square foot up to 300 square feet. Also, don't overlook mileage deductions if you drive for work. Keep a log of business-related trips - even driving to pick up supplies or meet clients counts. The standard mileage rate for 2025 is 70 cents per mile, which can really add up over the year. One more tip: consider getting a business credit card to keep all your business expenses separate from personal ones. Makes tax time SO much easier when everything is already organized.

As someone who went through a similar situation, I'd strongly recommend being very cautious here. The IRS has specific criteria for medical expense deductions, and gym memberships rarely qualify even with a doctor's recommendation. The key issue is that they view fitness facilities as having a "personal pleasure" component that disqualifies them as purely medical. For a gym membership to potentially qualify, you'd need: 1) A specific diagnosed medical condition (not just general health improvement), 2) A doctor's prescription (not recommendation) stating the facility is necessary for treatment, 3) Documentation that the treatment can't be performed elsewhere, and 4) Evidence you're using it solely for medical treatment. Since you're self-employed, remember you'd still need to itemize deductions and exceed the 7.5% AGI threshold for medical expenses. Given the audit risk others have mentioned and the strict IRS interpretation, you might want to focus on other legitimate medical deductions instead. Keep your doctor's documentation though - it could be useful for other related medical expenses.

Based on my experience as a tax professional, I have to echo what others have said - gym memberships are extremely difficult to deduct, even with a doctor's recommendation. The IRS has consistently ruled that health club memberships have too much "personal benefit" to qualify as pure medical expenses. However, since you mentioned you're self-employed, there might be a different angle worth exploring. If your back problems are directly related to your work (like if you have a desk job that caused the issues), you might be able to argue for a business expense deduction instead of a medical one. This would require documenting that the gym membership is primarily to address work-related health issues that affect your ability to perform your job. That said, this is still a risky deduction that could trigger scrutiny. The safest approach would be to focus on clearly qualifying medical expenses - your doctor visits, any physical therapy, prescribed medications, etc. These definitely count toward your medical expense total and are much less likely to raise red flags. Keep that doctor's documentation though - it might be useful if you end up needing specific therapeutic treatments that can only be done at certain facilities.

Great discussion here! I went through this exact same situation about 6 months ago when I started my corporate job while keeping my weekend Instacart deliveries. One thing I learned the hard way - don't underestimate your gig income when using any of these tools. I was conservative with my estimates and ended up owing about $800 at tax time. It's definitely better to overestimate and get a small refund than to owe money. Also, keep really good records of your gig work throughout the year. I use a simple spreadsheet to track weekly earnings from each platform, plus all my expenses (gas, car maintenance, phone mount, etc.). Makes everything so much easier when tax time comes around. The quarterly payment thing mentioned earlier is super important too. I set up automatic reminders in my phone for the due dates so I don't forget. Missing those can result in penalties even if you end up getting a refund when you file your return.

This thread has been incredibly helpful! I'm in a similar situation but with a twist - I'm starting a remote full-time job while continuing my weekend photography gig (wedding photography, not rideshare). From what I'm reading, the principles are the same regardless of the type of gig work, right? I should still use the Multiple Jobs Worksheet or the IRS estimator tool to figure out my W4, and I'll still need to make quarterly payments for the photography income since it's self-employment income with no automatic withholding. One question I have that I haven't seen addressed - does it matter that my gig work is more seasonal? Wedding season is basically March through October, so my income from photography varies dramatically throughout the year. Should I still spread the quarterly payments evenly, or adjust them to match my actual seasonal earnings? Also, thank you to everyone who shared those helpful tools and services. I've bookmarked several of them for when I inevitably get confused filling out all these forms!