This is such a helpful discussion! I'm new to the 529 world and had no idea about the distinction between application fees and enrollment fees. My daughter is a junior in high school, so we're just starting to think about college expenses. One question I have after reading through all these comments - what about college visit expenses? We're planning to visit several schools this spring and summer, and I'm wondering if things like campus tour fees or overnight stay programs count as qualified expenses? Some schools charge $25-50 for official visit programs that include tours, information sessions, and sometimes meals. Also, does anyone know if SAT/ACT prep courses or test fees themselves qualify? My daughter needs to retake the SAT and we're considering a prep course that costs $800. I'm assuming test prep doesn't qualify since it's pre-admission, but the actual test fees might be different? Thanks for all the great advice about documentation - I'm definitely going to start that spreadsheet now rather than trying to piece everything together later!

Thanks for sharing your experience with the 529 administrator update! It's great to see confirmation that enrollment fees ARE qualified expenses. I'm actually in a similar boat - my son is applying to colleges this fall and I was wondering about the same distinction. Based on all the helpful comments here, it sounds like the key is that timing matters a lot. Application fees before acceptance don't qualify, but once he's accepted and pays that deposit to secure his spot, that DOES count as a qualified 529 expense. One thing I'm still unclear on - what about things like housing deposits? If my son gets accepted and has to pay a separate $300 housing deposit to reserve a dorm room, would that be considered a qualified expense since it's required for attendance? Or does it fall into a different category since it's specifically for housing rather than enrollment? The documentation advice from everyone here is really helpful too. I'm definitely going to start tracking everything now rather than trying to sort it out later during tax season!

I'm a delivery driver too and am used Schedule C to deduct my expenses. One thing I want to clarify - meals are SOMETIMES deductible, but only in specific situations. If you're on a delivery that takes you out of town overnight (like some catering gigs do), then meals during that time are 50% deductible. But regular lunch during your local delivery shift isn't deductible at all. For clothing, I checked with my tax person and they said unless it's a uniform that can't be worn elsewhere, it's not deductible. My delivery company polo shirts with logos count, but jeans don't. Same with shoes - even if you use them just for delivery, they're not deductible if they're just regular sneakers.

As someone who's been doing delivery driving for over two years, I can share what I've learned about deductions through experience and working with a tax professional. For clothing, the key test is whether it's "ordinary street wear." If you can wear it outside of work without looking like you're in uniform, it's generally not deductible. So those jeans and regular t-shirts your roommate mentioned? Not deductible, even if you only wear them for deliveries. However, if you have branded shirts, jackets, or hats that clearly identify you as working for a delivery company, those typically qualify. For meals, your roommate is unfortunately wrong. The IRS considers meals during your regular work day as personal expenses, not business expenses. Being "in the food business" doesn't change this rule. You can't deduct your lunch just because you're delivering someone else's lunch. The good news is there are plenty of legitimate deductions you might be missing: your delivery bags, phone mount, car chargers, GPS devices, and even a portion of your cell phone bill if you use it for delivery apps. Plus, as others mentioned, mileage is huge - make sure you're tracking every business mile, not just the ones the apps show you. With $32k in earnings, these deductions can really add up, but stick to the legitimate ones to avoid any issues with the IRS.

Anyone else curious WHY tax software companies can't get this stuff right? I mean, Form 2441 is complicated but it's not THAT complicated. I spent hours trying to figure out why TurboTax and H&R Block gave me different childcare credit amounts last year. Ended up having to manually override things. The IRS instructions are super clear about FSA reductions!

This is exactly why I always recommend doing a manual check of Form 2441 when you have FSA involved! The math is pretty straightforward once you understand the logic - your total qualifying expenses of $6,718 minus the $483 FSA should give you $6,235 in eligible expenses for the credit calculation. The third software program giving you the higher credit is definitely wrong. You can't claim the full $6,718 in expenses when $483 was already paid with pre-tax dollars through your husband's FSA. That would be double-dipping on tax benefits, which the IRS specifically prohibits. I'd go with the calculation from your first two programs showing the $1,247 credit. Better to be conservative and correct than to claim too much and potentially face questions later. The $98 difference might seem small, but accuracy is key when it comes to tax filings!

You're overthinking this. Just print your state return from TurboTax and mail it in! When TurboTax rejects your federal+state combo electronically, you can still print the completed state forms and mail them to your state tax agency. I had to do this last year. Just make sure to sign the forms and include any payment if you owe taxes.

Hey NebulaNova! I've been through this exact nightmare myself. Here's what worked for me when I got stuck in the same federal-already-filed-but-need-state-only situation: Since you already paid for TurboTax and entered all your info, definitely try to use what you've got first. Go back into your TurboTax account and look for "Review" or "File" sections - there should be checkboxes where you can uncheck federal filing and only submit state. If you can't find it easily, their chat support is actually pretty helpful for walking you through this specific scenario. BUT if TurboTax gives you any more headaches, honestly just go with the print-and-mail option that Mei Lin mentioned. I ended up doing that when I couldn't get the electronic filing to work right. Print your completed state forms from TurboTax, sign them, and mail them to GA. It's old school but it works and you're already past the deadline stress anyway. Also, for future reference - Cash App Taxes really needs to step up their state return game. So many people run into this part-year resident issue with them!

This is a really comprehensive discussion! I'm dealing with a very similar situation and wanted to share what I learned after consulting with my CPA about this exact issue. The key thing my accountant emphasized is that the IRS cares about substance over form - meaning as long as you're properly reporting all income and following S Corp requirements, the fact that 1099s are issued in your personal name versus business name is just a paperwork quirk, not a fundamental problem. Here's what we're doing for my situation: 1) All contractor payments go directly into my business bank account, 2) I keep a simple log showing which 1099s were issued incorrectly to my personal name, 3) My S Corp reports all the income on Form 1120S regardless of whose name is on the 1099, and 4) I attach a statement to my personal return explaining that the 1099 income is being reported through my S Corporation. My CPA also mentioned that this is becoming increasingly common as more businesses use automated payroll systems that aren't set up to handle LLCs properly. The IRS sees this all the time now. One last tip - if you're doing significant contract work, consider asking clients to issue checks to your business name even if they insist on putting your personal name on the 1099. Most will accommodate this since it doesn't affect their reporting requirements.

This has been such an informative thread! As someone who's been wrestling with this exact situation for months, I really appreciate everyone sharing their experiences and solutions. I wanted to add one more resource that might be helpful - the IRS Revenue Ruling 2004-75 specifically addresses situations where income is reported under different names/entities. It essentially confirms what everyone here has been saying: as long as all income is properly reported somewhere in the tax system and you maintain proper documentation, the IRS is satisfied. One thing I learned from my tax attorney is to also keep copies of any emails or correspondence where you attempted to get the 1099 issued correctly. Even if the client refused, having that paper trail shows good faith effort on your part to handle things properly. For those still on the fence about S Corp election - I ran the numbers and even after factoring in payroll costs (~$600/year), extra CPA fees (~$800/year), and the administrative headache, I'm still saving about $4,200 annually in self-employment taxes on a $65K contract. The break-even point for me was around $50K in net income. Thanks to everyone who shared their real-world experiences - this is exactly the kind of practical guidance that's so hard to find elsewhere!