Your approach of detailed documentation with photos and ItsDeductible valuations is excellent! I've been doing similar clothing donations for years and can offer some practical insights. Regarding your question about splitting donations across tax years - this is absolutely legitimate and many tax professionals actually recommend it. The $500 threshold does trigger additional paperwork requirements, but it's not as daunting as it might seem initially. One strategy I've found helpful is to separate your items by condition and value. Donate your lower-value everyday items first (keeping under $500) and save any higher-value pieces (designer items, barely worn professional clothing, etc.) for a separate donation where you'll complete Form 8283. This way you maximize your deduction while minimizing complexity. Also consider timing - if you're close to year-end and already have significant itemized deductions locked in, it might make sense to push some donations to January to help with next year's taxes, especially if you expect your income or tax situation to change. The key is consistent, reasonable documentation. Your spreadsheet approach puts you ahead of most taxpayers, and the IRS generally respects thorough record-keeping. Don't let the $500 threshold scare you away from claiming legitimate deductions you're entitled to!

Your documentation approach is really thorough - taking photos and using ItsDeductible puts you in a great position regardless of which route you choose. I've been dealing with similar donation decisions and wanted to share a few practical considerations. The audit risk concern is understandable, but in my experience, the IRS is more focused on unreasonable valuations than properly documented donations over $500. Your detailed spreadsheet with conservative valuations actually demonstrates good faith compliance. One factor to consider is your time value. If splitting the donations saves you several hours of Form 8283 paperwork and you're comfortable with the slightly delayed deduction timing, that might be worth it. On the other hand, if you expect to have large donations regularly, getting comfortable with the Form 8283 process now could save hassle in future years. Also worth noting - if you do go over $500, you can group similar items on the form rather than listing each piece individually. So "men's business shirts (12 items)" with a total value is acceptable, which makes the paperwork much more manageable than it initially appears. Given that you're already itemizing and in a high bracket, you'll get the same tax benefit either way. I'd lean toward whatever approach gives you more confidence and peace of mind in your record-keeping.

Just my two cents, but I've been audited before and parking deductions were one of the things flagged. My advice is to be super conservative with this. If you're claiming the home office deduction already, trying to also claim the garage separately might raise red flags.

As someone who's dealt with similar home office deduction questions, I'd recommend being very methodical about this. The key is proper documentation and understanding which method gives you the better deduction. Since you're already claiming 15% of your home for business use, you have a few options for the parking: 1. Include it as part of your home office calculation (15% of the $285/month) 2. Use it as part of the actual expense method for your vehicle if you switch from standard mileage 3. Treat it separately based on documented business use percentage The safest approach is probably option 1 - just include it in your existing home office percentage. This keeps everything consistent and is less likely to raise audit flags. Whatever you choose, make sure you keep detailed records of your business trips vs. personal use. A simple spreadsheet tracking dates, destinations, and purposes of trips will go a long way if you ever need to justify the deduction. Also consider consulting with a new tax professional before making any major changes to your deduction strategy, especially given the audit concerns mentioned by others here.

For house hackers: Don't forget to take the 199A Qualified Business Income deduction for your rental activity! It's a 20% deduction on your qualified business income from the rental portion. This applies on top of your depreciation deductions.

Great discussion everyone! Just want to add one more important consideration for house hackers dealing with HVAC depreciation - make sure you're properly documenting the "placed in service" date for your depreciation calculations. Since you mentioned the system died and was replaced, the depreciation clock starts ticking from when the new HVAC system was installed and operational, not when you paid for it or when the old one failed. This matters for the MACRS half-year convention calculations. Also, keep detailed records of the installation invoice showing the breakdown between equipment costs and labor. Sometimes contractors will itemize things like ductwork modifications separately, which might have different depreciation schedules than the main HVAC unit itself. The IRS loves documentation during audits, especially for rental property deductions! One last tip: Consider getting a cost segregation study done if you're planning to acquire more rental properties. It can help identify components that qualify for faster depreciation schedules beyond just the HVAC system.

For what it's worth, I'm a payroll specialist and we sometimes leave Box 18 blank when all wages are subject to local tax. It's not technically incorrect - just confusing for tax software. The correct approach is to enter the same amount as Box 1 (federal wages) unless you have specific local exemptions. The reason tax software requires Box 18 to be >= Box 19 is because you can't have local tax withheld on $0 wages logically.

Thanks everyone for all the helpful advice! I ended up following Mateo's suggestion and entered my Box 1 amount into Box 18, and it worked perfectly. The tax software accepted it and I was able to complete my filing. For anyone else dealing with this issue - it really is as simple as copying your federal wages (Box 1) into the local wages field (Box 18) when it's left blank. Mei's explanation as a payroll specialist really helped confirm this was the right approach. I was so worried about entering something that wasn't explicitly printed on my W-2, but it turns out this is totally normal and expected. My return has already been accepted by the IRS, so I can confirm this solution works without causing any problems. Thanks again to this community for helping me get unstuck!

Just wondering - has anyone had issues with their refund after filing a superseding return? I'm in a situation where I'd get a bigger refund with the corrected return and wondering if it complicates or delays things?

I went through this exact same situation two years ago and can confirm what others have said about the process. One thing I'd add that saved me a lot of stress - when you write "SUPERSEDING RETURN" at the top, use a red pen or marker if you're mailing it in. It makes it much more visible to the processors. Also, keep copies of EVERYTHING. I mean your original return, the superseding return, all your supporting docs, and even the envelope you mail it in (take a photo). The IRS processed mine correctly, but having all that documentation gave me peace of mind. One more tip - if you're close to the deadline, send it certified mail with a return receipt. That way you have proof it was delivered before April 15th, which is crucial since superseding returns must be filed by the original deadline.