Has anyone looked into the IRA Qualified Charitable Distribution option? If you're over 70.5 years old, you can donate directly from your IRA to a charity and it counts toward your Required Minimum Distribution without increasing your taxable income. You don't itemize it because it's never counted as income in the first place. Might be something to consider for older taxpayers facing this issue.

I completely understand your frustration! I was in almost the exact same situation last year with about $7,200 in charitable donations but only $23,500 total itemized deductions. After researching extensively, I can confirm what others have said - those charitable deductions are essentially "lost" for tax purposes if you take the standard deduction. There's no carryforward provision unless you exceed 60% of your AGI (which at $380k would be $228k in donations - way more than your $8,500). However, I did learn about the "bunching" strategy that's been mentioned. Instead of donating $8,500 every year, you could potentially donate $17,000-20,000 in alternating years. This way you'd itemize every other year (assuming your other deductions stay consistent) and take the standard deduction in the off years. With your income level, you might also want to consider donating appreciated stock or mutual funds instead of cash if you have any. You avoid capital gains tax AND get the full market value deduction. Just make sure you've held the securities for more than a year to get long-term capital gains treatment. The Donor Advised Fund suggestion is also worth exploring - it lets you make a large contribution in one year for the tax benefit, then distribute to charities over multiple years as you see fit.

Another option: you can actually get your wage and income transcript directly from the IRS website which will show any 1099s filed for you. Go to IRS.gov and search for "Get Transcript Online." If nothing shows up for that company, they probably haven't filed it yet. Also, keep in mind you're supposed to get your 1099s by January 31st. If companies don't comply, they can face penalties. The IRS actually takes this seriously because they want the tax revenue from contractors.

Had this same problem last year. What I did was file Form 8919 "Uncollected Social Security and Medicare Tax on Wages" along with my return. This is for when you were treated as an independent contractor but should actually have been an employee. The benefit is you only pay the employee portion of FICA taxes (7.65%) instead of the full self-employment tax (15.3%). Check out the criteria on the form - if you were essentially working like an employee (they controlled your schedule, provided equipment, etc.), this might apply to you and save you some money.

Has anyone tried negotiating an Offer in Compromise? I've heard you can settle for pennies on the dollar but not sure if that's just marketing hype from those tax relief companies.

I went through something similar with about $25k in back taxes a couple years ago. Here's what I learned: 1. **Don't panic** - The IRS actually wants to collect what you owe, so they're motivated to work with you rather than let it sit unpaid. 2. **Start with an installment agreement** - For your amount ($28k), you can likely get a 72-month payment plan online. That would be roughly $390/month, but you can often negotiate lower payments if you can show financial hardship. 3. **Consider Currently Not Collectible status** if you truly can't afford payments right now. This pauses collection activities while you get back on your feet financially. 4. **File any missing returns immediately** if you haven't already - the IRS can't work with you on payment plans until all required returns are filed. 5. **Avoid most tax relief companies** - they charge thousands for what you can do yourself. The legitimate ones that might be worth it are few and far between. The key is being proactive. Once you have an agreement in place, the stress drops dramatically. I was able to get my monthly payment down to something manageable and even got some penalties waived for first-time non-compliance. Don't let this consume you - there are definitely solutions available.

Went through this exact situation last year. The Tax Court has consistently upheld that the date of mailing a properly written check is the date of contribution, provided it's eventually cashed. Treasury Reg. 1.170A-1(b) is definitely your friend here. I'd try one more approach with the charity - ask to speak with their Director of Development or CFO, not just the regular receipting staff. Explain that while you understand their internal cutoff policies, the tax law is clear about when a donation is considered made. If they still won't budge, document everything and claim it on your 2022 return anyway. Just be sure to keep all your evidence (certified mail receipt, copy of the check, their 2024 acknowledgment, and your communications requesting correction).

I've been following this discussion and wanted to add my experience as someone who dealt with a very similar situation. The advice here about the mailbox rule and Treasury Regulation 1.170A-1(b) is spot on. What worked for me was being persistent but polite with the charity. I called their main number and asked to speak with someone in their finance or development department who handles tax compliance, rather than just the general receipting staff. I explained that their internal deadlines don't override IRS regulations for donor deductibility. I also mentioned that issuing incorrect tax documentation could potentially create problems for both the donor and the organization if questioned by the IRS. Most nonprofits want to maintain good relationships with donors and avoid any compliance issues, so framing it this way often gets better results. If you do end up claiming it on your 2022 return with the documentation you have, make sure to keep a copy of your letter or email to the charity requesting the correction. This shows good faith effort to get proper documentation and strengthens your position if there are any questions later. The bottom line is you're absolutely right about the tax treatment - don't let their accounting convenience override your legitimate deduction rights!

I went through something very similar when I sold my Magic: The Gathering collection last year. Had about $8,000 in sales but definitely sold most cards at a loss from what I originally paid. Here's what I learned: You're right that you generally won't owe income tax on personal items sold at a loss, but you still need to handle the 1099-K properly. I created a simple spreadsheet with three columns: Item Description, Estimated Original Cost, and Sale Price. For items where I couldn't remember exact prices, I used current retail prices from when I bought them (you can often find historical pricing data online for video games). The key is being reasonable and consistent with your estimates. Don't lowball the sale prices or inflate the original costs, but honest estimates based on your memory and research are acceptable. I also took photos of my collection before selling and kept screenshots of completed eBay listings as additional documentation. When tax time came, I reported the 1099-K income but offset it by showing these were personal items sold at a loss. No issues with the IRS at all. The important thing is having some documentation of your thought process, even without original receipts.

Great question! For video game historical pricing, I found PriceCharting.com to be incredibly helpful - they have historical data going back years for most games. You can also check Wayback Machine snapshots of GameStop, Best Buy, or Amazon for retail prices from specific time periods. For really old games, I looked at forums and collector sites that discussed original MSRP. Regarding the offset, I used Schedule 1 and reported the 1099-K amount on line 8i "Other Income" with a description like "eBay sales - personal items." Then I attached a statement showing my cost basis calculations and noting these were personal items sold at a loss, so the net taxable income was $0. Some tax software makes this easier than others - TurboTax let me add explanatory text, but with other software I had to attach a separate document. Since your collection is worth $13,500, I'd definitely recommend keeping detailed records and maybe even consulting with a tax professional for the first year you do this. The documentation approach I described worked well for my $8K situation, but with your higher dollar amount, having professional guidance on the proper reporting method could save you headaches later. The key is being thorough and transparent about your methodology.