Don't forget to check reviews! Google "[company name] scam" and show her results. When my grandma almost fell for one, I showed her their 1.2 star BBB rating and pages of complaints from seniors who lost thousands. Also search for their company on the FTC website - many have been sued for deceptive practices. Just Google "FTC tax relief scam [company name]" and show her the government actions against them. The AARP website has a great article about tax scams targeting seniors too - might be worth printing that out for her.

I'm going through this exact situation with my elderly aunt right now. What really helped was sitting down with her and going through the actual numbers together. I asked her to show me the letter from the tax relief company and we calculated what she'd actually save versus what they were charging. Most of these companies charge $2,000-$5,000 upfront, but when you look at what they're promising to save, it often doesn't even break even. In my aunt's case, they wanted $3,500 to "reduce her tax burden" when she actually gets a refund every year! I also found it helpful to remind her that the IRS has payment plans and their own hardship programs that are FREE if someone truly can't pay. No legitimate tax professional should be asking for thousands upfront before they've even reviewed your situation. The fear tactics are really what get to them. Maybe try reassuring your mom that being current on her taxes actually puts her in a great position - she's doing everything right and doesn't need "protection" from anyone.

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.

Just throwing this out there - might also wanna check that ur state withholding account has the right address too! When I regstered mine the info got messed up somehow between the state and federal systems. Ended up with letters going to 3 different addresses 🤦‍♂️ Had to fix each one separately.

This exact scenario happened to my consulting business last year! When I registered for state payroll withholding, it definitely triggered an old CP148A notice - turns out the IRS had been sitting on it since I had filed a change of address form months earlier but never received confirmation. The key thing is that CP148A notices are just informational - they're confirming an address change, not demanding any action. But the 2020 date is definitely weird and suggests a system error or backlog issue. I'd recommend calling that Business & Specialty Tax Line number mentioned earlier AND filing Form 8822-B just to be safe. When you call, specifically ask them to verify what address they have on file for all your business tax accounts (income tax, payroll tax, etc.) because sometimes they don't sync up properly between different IRS systems. Also, double-check your state withholding account registration to make sure the address there matches what you want the IRS to have. These cross-system triggers can create a domino effect if the addresses don't align perfectly.

Small correction to what some others have said - if you're using a property management company that charges you a commission when they place tenants AND a monthly management fee, check your contract carefully. Sometimes these placement fees are actually prepaid management fees and should be amortized over the lease term rather than deducted immediately. This came up in my audit last year!

Thanks everyone for all the helpful info! This is exactly what I needed to understand. Just to make sure I've got this right - when I buy the rental property, any commission I pay gets added to my basis and I recover it through depreciation over 27.5 years. But when I pay a realtor to find tenants, that's a current year deduction on Schedule E. One follow-up question though - what if I use the same realtor for both? Like if my buyer's agent also offers property management services and will help me find tenants later. Do I need separate contracts or invoices to make sure the IRS can see which commission is for what purpose? Also @McKenzie Shade, thanks for the heads up about the new reporting requirements! I definitely want to make sure I'm compliant from the start. Where can I find more info about these draft forms?