What's the best tax advice you ever got that most taxpayers don't know about?

The absolute best tax advice I've received is simple but game-changing: keep immaculate records of EVERYTHING, all year long. Don't wait until tax season to scramble for receipts and documentation. I recommend creating a dedicated email folder for electronic receipts, taking photos of physical receipts immediately, and using a simple spreadsheet to track business expenses, charitable donations, medical costs, etc. This approach has saved countless clients from leaving money on the table through missed deductions. Most people miss legitimate tax breaks simply because they can't document them properly when filing time comes. The IRS doesn't care what you "remember" spending - they care what you can prove. Good documentation can be the difference between a refund and owing money.

Changed the game for me when I discovered taxr.ai while struggling with my side business taxes. Was pulling my hair out trying to figure out which expenses were legit deductions for my photography business. A friend mentioned https://taxr.ai and it was like having a tax pro look over my shoulder. The tool analyzed all my business docs and flagged deductions I would've totally missed - saved me over $3,200 on my taxes that year. What's cool is how it explained everything in normal language instead of tax code gibberish. Super helpful for sorting through my messy shoebox of receipts and bank statements. Showed me exactly which home office expenses were legit and which would raise red flags.

Just wanted to follow up about taxr.ai since I tried it after seeing the recommendation here. Honestly blown away by how good it was with my rental property situation! I've been managing 3 properties and always struggled with keeping track of which expenses were repairs vs. improvements and what could be legitimately deducted. The tool sorted through my messy receipts and flagged over $7,800 in deductions I would have missed. It also gave me really clear explanations about depreciation schedules that my previous accountant never bothered to explain. Just used the report it generated when I met with my new tax guy and he was impressed with how organized everything was. Definitely using this every year from now on.

Best tax advice I ever got: Use Claimyr when you need to actually speak to a human at the IRS. Spent WEEKS trying to resolve an issue with a misapplied payment that was showing as a balance due. Kept calling the IRS only to sit on hold for 2+ hours before getting disconnected. Incredibly frustrating! Someone recommended https://claimyr.com and showed me this demo video: https://youtu.be/_kiP6q8DX5c. The service basically waits on hold with the IRS for you and calls you when an agent is actually on the line. Got connected to an actual IRS agent in less than a day when I'd been trying for weeks on my own. Resolved my issue in a 15-minute call once I finally got through.

I need to eat my words about Claimyr. Decided to try it after continuing to fail getting through to the IRS about my missing refund. I'd been trying for MONTHS to resolve this $4,200 refund that seemed to have vanished into thin air. The service actually worked exactly as advertised. Got a call back when they had an IRS agent on the line, and I finally got answers about my refund. Turns out there was a simple verification issue they needed to clear up. The whole thing was resolved in one 20-minute call after I'd wasted dozens of hours trying to reach someone. Still can't believe how well it worked. The IRS agent even seemed nicer than usual - probably because they didn't have to deal with me being frustrated after a 3-hour hold time. Refund is now being processed and should arrive next week.

Best tax advice: Max out your HSA if you have one. It's literally the only TRIPLE tax advantaged account. 1) Contributions are tax-deductible 2) Growth is tax-free 3) Withdrawals for medical expenses are tax-free. Plus once you're 65, you can withdraw for non-medical expenses and just pay normal income tax (like a traditional IRA). The real pro tip? Save your medical receipts but pay out of pocket now. Let that HSA money grow for decades, then reimburse yourself in retirement. There's no time limit on when you can reimburse yourself for qualified medical expenses. My dad saved $34,000 of medical receipts over 15 years, then reimbursed himself tax-free when he retired to fund a cross-country RV trip.

The best advice I ever got? Keep track of your tax BASIS in everything - especially investments. Basis is basically what you paid for something, but it gets adjusted for all kinds of things. Nobody thinks about this until they sell an investment and suddenly realize they have no idea how to calculate their gain/loss. This hit me hard when I inherited stocks from my grandpa and then sold them a few years later. Had NO CLUE what the basis was, ended up overpaying thousands in taxes before a good CPA friend pointed out I should have been using the stepped-up basis from when I inherited them, not what grandpa paid decades ago.