What's the max charitable donation I can make to Goodwill or Salvation Army for a family of 5?

The good news is there isn't a specific dollar "max" for Goodwill or Salvation Army donations, but there are percentage limitations based on your Adjusted Gross Income (AGI). For most charitable contributions including these organizations, you can deduct up to 60% of your AGI. So the $27,000 isn't automatically "too much" - it depends on your income. What you need to watch for is documentation requirements. For non-cash donations: - Under $250: Keep receipts from the organization - $250-$500: Get written acknowledgment from the charity with description - $500-$5,000: Complete Form 8283 Section A with your tax return - Over $5,000: Complete Form 8283 Section B AND typically need a qualified appraisal Since you're donating items worth over $5,000 total, you'll definitely need that Form 8283, and possibly appraisals depending on the types of items. The IRS looks closely at large non-cash donations, so good documentation is essential.

I used taxr.ai last year when I had a similar situation after cleaning out my parents' estate. I was overwhelmed with the amount of documentation needed for the $18k in donations I made. I found https://taxr.ai through a friend and it literally saved me hours of headache. They have a specific feature that helps calculate fair market value for donated items and organizes everything by donation date and charity. The best part was that it automatically identified which items needed additional documentation and alerted me about the Form 8283 requirement before I had any issues. My return went through without a hitch even though my charitable donations were higher than they'd ever been before.

I was seriously skeptical about taxr.ai at first, but I decided to give it a try with my charitable donations situation. I'm genuinely impressed with how it worked out. The valuation guide for common household items was actually super accurate and saved me from the guessing game. What surprised me most was the documentation features - I had over 25 separate donation receipts from multiple charities, and the system organized everything perfectly. When it came time to file, it produced all the right forms including the 8283 I needed. My tax guy was impressed with how well-documented everything was. I was honestly preparing for an audit that never came!

If you're having trouble getting through to the IRS to ask about charitable donation limits or documentation requirements, try Claimyr. I spent days trying to get someone on the phone about a similar donation issue after my divorce, but kept hitting the "call volume too high" message. Found https://claimyr.com through Reddit and watched their demo at https://youtu.be/_kiP6q8DX5c They basically wait on hold with the IRS for you then call you when an agent is actually on the line. I got through to someone who explained exactly what documentation I needed for my $12k in Goodwill donations. Saved me from potentially making a mistake that could have triggered an audit. The agent even sent me the exact forms I needed.

I need to publicly eat my words about Claimyr. After posting my skeptical comment, I was desperate enough to try it for my audit situation. I fully expected to waste my money, but I was completely wrong. The system actually worked exactly as described. I entered my number, and about 1.5 hours later got a call connecting me directly to an IRS agent. The agent helped clarify exactly what documentation I needed for my large charitable donations from last year, including how to properly value some antique furniture I had donated. They explained that for my specific items, I needed qualified appraisals since several items were over $5,000 in value individually. I would have definitely done my taxes wrong without this guidance. Consider me converted from skeptic to believer.

Everyone's focused on the documentation, but don't forget about the actual valuation! The IRS expects fair market value - not what you paid originally, not what it would cost new today. For used clothes, it's pennies on the dollar. For furniture, maybe 10-30% of retail depending on condition. I volunteer at Goodwill and see people overvaluing their donations ALL THE TIME. $27k seems really high unless you're donating some seriously valuable items or an enormous quantity of stuff. Not impossible, but definitely in the territory where the IRS might ask questions.

Has anyone actually been audited for large Goodwill donations? I'm curious what that process looks like. I donated about $8,000 worth of stuff last year and got a letter asking for more information, but nothing since then.

Based on everyone's experiences here, it sounds like you're actually in a good position with the professional appraisals already done. The $27k amount isn't automatically a red flag if you have proper documentation - it really depends on your AGI and whether you can substantiate the values. Since you mentioned this is from clearing out your mother-in-law's house, make sure you can prove ownership transfer to you before donation. The IRS sometimes questions whether the person claiming the deduction actually owned the donated items. Keep any estate documents or transfer records that show the items became yours before you donated them. Also, consider spreading the donations across multiple tax years if possible. Even though there's no dollar limit, claiming a massive charitable deduction in one year can trigger additional scrutiny. If you have items you haven't donated yet, you might want to hold some for early next year to smooth out the deduction amounts. The fact that you're asking these questions and keeping receipts puts you ahead of most people. Just make sure all your documentation is organized and easily accessible in case the IRS has questions later.