Has anyone actually compared what they get using the IRS calculator vs tracking all your purchases? I'm wondering if it's worth the effort of keeping every receipt or if the IRS calculator is generally pretty accurate?

I've been dealing with this exact same issue! What I ended up doing was creating a simple spreadsheet to track my major purchases throughout the year while waiting for the IRS calculator to be updated. I set up columns for date, store, purchase amount, and sales tax paid. The key insight I learned is that you don't need to track EVERY single purchase - focus on the big ones. Things like appliances, electronics, furniture, car repairs, etc. For day-to-day purchases like groceries and gas, the IRS table estimates are usually pretty close. I also discovered that some credit card companies and banks categorize your spending in their year-end summaries, which can help you identify categories where you might have paid significant sales tax. It's not perfect, but it gave me a good starting point for estimating until the official tools are available.

Another tip about capital losses - watch out for mutual fund distributions at year-end! I got burned last year because I was showing a paper loss on a mutual fund, so I sold it to harvest the loss in December. But the fund had a capital gain distribution a week later that I would have received as a shareholder. Since I had sold, I avoided that distribution, which would have increased my cost basis. But what I didn't realize is that the NAV (price) of the fund dropped by the exact amount of the distribution right after the ex-div date. So I ended up selling at an artificially low price and my tax loss was smaller than it would have been if I'd waited until January! Always check distribution schedules before harvesting losses in mutual funds.

You're absolutely right that tax-loss harvesting isn't some magical money-making strategy - it's really just basic fairness in the tax code. But there are a few strategic elements that make it more powerful than it initially appears. The biggest one that hasn't been fully emphasized is the timing flexibility it gives you. Instead of being forced to pay taxes on gains in the year they occur, you can strategically realize losses to offset them. This is especially valuable in volatile markets where you might have paper losses available to harvest. Another key benefit is that it allows you to "reset" your cost basis on investments you want to keep long-term. You can sell an underperforming position for the tax loss, wait 31 days to avoid wash sale rules, then buy it back at the new (hopefully lower) price. You've locked in the tax benefit while maintaining your investment thesis. The $3,000 ordinary income deduction is also more valuable than people realize because it's "above the line" - meaning it reduces your AGI, which can help you qualify for other tax benefits or avoid phase-outs that kick in at higher income levels. So while you're correct that it's not "gaming the system," the strategic timing and flexibility aspects make it a legitimate and valuable tax planning tool beyond just the basic math.

Does anybody know if filing for an extension changes anything about the statute of limitations for unfiled returns? Like if I filed for an extension but then never actually submitted the return, does that at least buy more time?

This is such an important topic that doesn't get enough attention! I learned this the hard way when I had to deal with some unfiled returns from my freelance work years ago. The "no statute of limitations" rule for unfiled returns is absolutely real and can be terrifying. One thing I'd add to the great explanations here is that even if the IRS doesn't actively pursue old unfiled returns, they can still create problems down the road. For example, if you ever need to apply for certain loans, professional licenses, or government positions, having unfiled returns in your history can be discovered during background checks and cause major issues. The key takeaway is: if you have unfiled returns, don't wait hoping the problem will go away. It won't. The sooner you address it, the better off you'll be. Even if you owe money, getting into compliance stops the clock on additional penalties and interest, and the IRS is often willing to work out payment plans once you're back in the system.

9 One thing nobody has mentioned: KEEP ALL YOUR RECORDS! The IRS requires you to keep a diary or log of all your gambling activities if you're claiming losses. This includes: - Date and type of gambling - Name/location of gambling establishment - Names of other people with you while gambling (if applicable) - Amounts won and lost If you get audited without these records, your loss deductions can be disallowed!

14 Also worth mentioning - gambling winnings are subject to different withholding requirements. If you win over certain thresholds (like $5,000 in a lottery), taxes should be withheld immediately. But for most online betting apps, they don't withhold taxes automatically, which is probably why you're in this situation.

Hahahaha I laughed at "having them all prepare my returns"... bro do u know how much tax prep COSTS? You're gonna pay like $300-500 at EACH place just to compare. Seems like an expensive experiment when you could just use free online software and do it yourself!

I actually work for the IRS (though obviously speaking for myself here, not the agency), and I can confirm this is completely legal. We don't care how many preparers you consult before filing - we only care that you file ONE accurate return. That said, a few professional observations: If you're getting wildly different refund amounts, that's concerning. The tax code is the tax code - legitimate preparers working with the same facts should get similar results. Big differences usually mean either 1) someone found deductions others missed (good), 2) someone is being overly aggressive with questionable positions (bad), or 3) there's an actual error somewhere. My advice? If you do this, ask each preparer to walk you through their major deductions and credits line by line. Don't just go with the biggest refund - go with the one who can best explain and justify their positions. Trust me, dealing with an audit because someone took aggressive stances to inflate your refund is way worse than getting a smaller legitimate refund upfront. Also, most preparers charge whether you file with them or not, so this could get expensive fast. Consider it an investment in understanding your tax situation better rather than just refund shopping.