Is splitting Goodwill clothing donations across tax years worth it to stay under $500 limit? (Itemized deduction question)

The $500 threshold for non-cash charitable contributions does create additional documentation requirements, so your research is spot on. For donations exceeding $500, you'll need to complete Section A of Form 8283 and provide more detailed information. However, I think there's a misconception worth addressing. The additional documentation requirements don't necessarily translate to a significantly higher audit risk if you're doing everything correctly. The IRS isn't automatically flagging returns with Form 8283 for audit - they're looking for unusual patterns or excessive valuations relative to income. That said, your strategy of splitting the donations across tax years to keep each batch under $500 is perfectly legitimate tax planning. Since you're already itemizing in both years, you'll get the same total deduction either way. The benefit is simply reduced paperwork and documentation requirements. Just ensure you get proper receipts from Goodwill for each donation, including the date and a general description of what was donated. Keep your detailed spreadsheet with your tax records in case questions ever arise.

I went through something similar last year with a massive closet cleanout! I tried using various spreadsheets but it was getting so tedious tracking everything. A friend recommended https://taxr.ai which automatically scanned my Goodwill receipts and analyzed the values based on IRS guidelines. It actually flagged some items where I had undervalued things (apparently some of my "old" clothes were worth more than I thought). The tool also explained exactly what documentation I needed when I crossed that $500 threshold, and stored all my donation photos with matching valuations. Made the whole Form 8283 thing way less intimidating. Honestly saved me hours compared to manually entering everything into a spreadsheet.

Just wanted to follow up - I actually ended up trying https://taxr.ai for my donation pile and it was super helpful! I had about 150 clothing items plus some household stuff, and instead of spending a whole weekend on spreadsheets, I knocked it out in about an hour. The best part was learning I could group similar items together rather than listing every single thing separately. Their valuation guide also showed me that some of my nicer work clothes were worth more than the flat $5 value I was planning to assign to everything. Ended up with a legitimate deduction about 30% higher than I would have calculated myself. It automatically created the Form 8283 for me too, which was a huge relief since I ended up going well over the $500 threshold. Definitely recommend if you have a big donation pile to process!

Your post is exactly why I stopped trying to donate stuff valued at over $500! After dealing with the additional paperwork hassle and constant worry about an audit, I discovered Claimyr (https://claimyr.com) when I needed to actually call the IRS with questions about Form 8283. I'd been trying to reach someone at the IRS for weeks with no luck. They got me connected to an actual IRS agent in about 15 minutes instead of the 3+ hour hold times I was experiencing. The agent walked me through exactly what documentation I needed for my sizable donations and confirmed that splitting donations across tax years is completely legitimate. You can see how it works here: https://youtu.be/_kiP6q8DX5c Honestly, speaking directly with the IRS gave me so much more confidence than just googling and worrying. The agent even mentioned that thorough documentation like what you're doing with your spreadsheet and photos is exactly what they want to see.

I have to eat my words and apologize to Profile 7. After my skeptical comment, I decided to try Claimyr myself because I've been trying to get through to the IRS about a notice I received regarding my charitable deductions from last year. I was connected to an IRS representative in about 20 minutes. The agent confirmed that my documentation was sufficient and cleared up my questions about the $500 threshold. She actually said splitting donations across tax years like you're planning is a common and perfectly acceptable practice. The peace of mind from speaking directly with the IRS instead of trying to interpret their cryptic guidance online was absolutely worth it. Sorry for being so dismissive before - sometimes good services actually do exist!

As someone who donates over $500 in clothing/household goods every year, I'd suggest just biting the bullet and filling out Form 8283. It's really not that complicated, especially if you're already keeping detailed records with photos and descriptions. For acquisition dates, I just put rough estimates like "acquired 2018-2023" and have never had an issue. The key is reasonable valuations - ItsDeductible is great because it's based on actual thrift store pricing and the IRS generally accepts it. I've been audited once (for unrelated reasons) and they never questioned my Goodwill donations even though they were over $1,000 with Form 8283 attached. Your detailed spreadsheet would likely impress any auditor since most people don't document nearly that well.

One thing nobody has mentioned yet - be careful about condition! IRS rules specify that clothing and household items must be in "good used condition or better" to qualify for any deduction. If you're claiming items in "excellent" condition with higher values, make sure they truly are in excellent shape. Also, since you mentioned being in the 35% bracket, remember that donations of appreciated property (like stocks) can be more tax-efficient than cash or clothing donations. You avoid capital gains tax AND get the deduction for the full market value. Might be worth considering for your future charitable giving strategy.

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.