Remember that gambling income is taxable even if you didn't get a W2G form. The IRS requires you to report ALL gambling winnings, even small amounts. Player cards at casinos can also track your activity.

The IRS gets copies of all W-2G forms that casinos issue for winnings over $1,200 (slots/bingo) or $5,000 (poker tournaments). Your transcript will definitely show these reported amounts even before you file your return. If you had $50k in wins, that's likely already in their system. Best to get your transcript now and see exactly what they have on file - you can request it free directly from IRS.gov. Don't risk penalties by underreporting what they already know about.

Doesn't anyone use digital storage anymore?? I scan everything into Google Drive and shred the originals. Been doing this for 10+ years now. I have a folder for each tax year and subfolders for W2s, property tax, etc. No more paper clutter and I can find stuff instantly when needed.

As someone who went through this exact decluttering process last year, I'd recommend creating a simple spreadsheet to track what you're keeping vs. shredding by year. The 3-year rule is generally safe for most people, but I kept 7 years worth just for peace of mind after reading about those audit extension scenarios. One tip that saved me hours: invest in a decent cross-cut shredder if you're going to tackle years of returns. My little strip-cut shredder died halfway through 2015's paperwork! Also, don't forget to shred any old bank statements or credit card statements from those same years - they often have account numbers that could be useful to identity thieves. For what it's worth, I found the decluttering process oddly satisfying once I got into a rhythm. Just make sure you double-check for any documents related to ongoing issues (like home improvements or investments) before you shred!

Have you checked your child's credit report? If someone has your child's SSN, they might be using it for more than just taxes. How did you discover that someone else claimed your child? Did you get a rejection when trying to e-file, or did you receive a notice from the IRS?

This is such a frustrating situation! I went through something similar when my neighbor's ex-wife claimed my daughter by mistake (they have the same first name). Here's what I learned from that experience: 1. Don't panic about the refund delay - yes, it will take longer, but you WILL get your money eventually 2. Gather every piece of documentation you have showing your child lives with you - school enrollment, medical records, daycare receipts, etc. 3. When you paper file, include a cover letter explaining the situation clearly 4. Keep copies of everything you send The most important thing is to act quickly. The IRS will eventually sort this out, but the sooner you get your paperwork in, the sooner they can start the review process. In my case, it took about 4 months total, but I got my full refund plus interest for the delay. Stay strong - you're the rightful parent and the system will work in your favor!

I've been following a similar strategy for about 2 years now, overpaying by roughly $18K annually. One thing that's given me peace of mind is working with a tax professional who helped me establish a defensible estimation methodology. What we do is create quarterly projections that account for variable income scenarios - like potential bonuses, freelance work, or investment gains that might materialize. I document these projections each quarter, showing how I arrived at my estimated payment amounts. Sometimes the income materializes, sometimes it doesn't, but the important thing is having a reasonable basis for each payment. The processing fees (around 1.9%) are definitely worth it when you're hitting signup bonuses that can be 15-20% returns in just a few months. Just make sure you're not putting all your overpayments on one card or making it too obvious that you're manufactured spending. My advice would be to treat this as legitimate tax planning first, credit card optimization second. Keep good records, vary your amounts somewhat year to year, and make sure you can articulate why your estimates led to overpayments if ever asked. The IRS isn't going to penalize you for being conservative with your tax planning.

I've been considering this strategy myself and appreciate all the insights here. One additional angle I'd suggest is looking at safe harbor rules for estimated taxes. If you pay either 100% of last year's tax liability or 110% (for higher income earners), you're automatically safe from underpayment penalties regardless of how much you actually owe. This gives you a legitimate framework for "conservative" estimates that could result in systematic overpayments. You could base your estimated payments on projections that ensure you hit these safe harbor thresholds, and if your actual income ends up lower, the overpayment becomes a natural byproduct of following IRS safe harbor guidelines. The beauty of this approach is that you're literally following an IRS-recommended strategy for avoiding penalties. It's hard for them to question a methodology they explicitly endorse, even if it results in consistent overpayments when combined with credit card optimization. Just make sure to document your safe harbor calculations each year to show you're following established tax planning principles rather than arbitrary overpayment amounts.

I'm in the middle of my OIC process and the waiting is brutal!!! Submitted everything 5 months ago and still showing as "pending" whenever I check the status online. Does anyone know if calling actually speeds anything up?

I went through the OIC process last year and it was one of the most stressful but ultimately rewarding experiences dealing with the IRS. My situation was similar to yours - owed about $38,000 due to business failure and medical issues. A few key things I learned: First, be absolutely honest and thorough with your financial documentation. The IRS will verify everything, and any inconsistencies will delay or kill your application. Second, don't underestimate how long it takes - mine took 14 months from start to finish, with multiple requests for additional paperwork. I did use a tax professional for the initial application, which cost me $3,500, but it was worth it for the peace of mind. They helped me calculate a realistic offer amount ($11,200 for my $38,000 debt) and made sure all the forms were filled out correctly. One thing nobody tells you - during the application process, the IRS stops collection activities, which was a huge relief. No more threatening letters or calls. Just be prepared for the emotional rollercoaster of waiting months without updates. The acceptance letter arriving was one of the best days of my life. Don't give up hope - if your financial situation truly warrants it, the program can work. Just be patient and meticulous with your paperwork.