7 I tried using that estimator but got confused halfway through. It asked for projected deductions and I had no idea what to put. Do you just guess? Or is there a way to figure out what deductions they'll have for this year?

11 For the deductions section, you can use last year's deductions as a starting point if your situation hasn't changed much. If your parents take the standard deduction (which most people do now with the higher amounts), you can just select that option without itemizing. If they do itemize, have them look at Schedule A from last year's return and use those figures as estimates, adjusting for any known changes (like if they paid off their mortgage or expect higher medical expenses this year).

16 Wait, so even if they pay everything they owe by the tax deadline, they can still get penalties if they didn't pay enough during the year?? That seems really unfair!

Does the spouse need to file anything special along with the return when they mark the other person as deceased? Like a death certificate or anything official?

For a joint return where one spouse is deceased, you generally don't need to submit a death certificate with the return itself. You simply write "DECEASED" after the deceased spouse's name at the top of the return, and include the date of death. If the surviving spouse is filing as the deceased taxpayer's personal representative, they should sign the return and write "Filing as surviving spouse" in the signature area. For more complex situations involving larger estates that require Form 706, additional documentation would be needed, but for typical joint returns, the notation is sufficient.

So sorry for your loss. I went through this with my husband last year. Another tip: request a tax transcript from the IRS for the past few years. Sometimes there are refunds or issues you didn't know about, and it gives you a complete picture of what the IRS has on file.

So if someone received notices but still didn't file for like 5+ years, could that be considered "willful" by itself? Or do they need other evidence?

Repeated failure to respond to notices does strengthen the case for willfulness, but typically the IRS still looks for additional factors beyond just ignoring notices. The government must prove beyond reasonable doubt that you deliberately intended to violate a known legal duty. Evidence they might look for includes patterns like filing in years with refunds but not in years when you'd owe, taking active steps to conceal income, or making statements to others about intentionally not filing. Simply being disorganized, even for many years, usually results in substantial penalties but not criminal prosecution. That said, the longer the pattern continues, especially after direct contact from the IRS, the riskier the situation becomes.

You can use TurboTax for prior years but you'll need to buy the specific software for each tax year separately - they sell previous year versions on their website. But you can't e-file past years, you'll have to print and mail them. I did this for 3 years of back taxes and it worked fine, just time-consuming.

Yes, we did call the police first! They came out and documented it, put one of those orange stickers on it, and told us we needed to wait 72 hours before having it towed. We followed all the proper channels. The police report actually said the car was reported stolen in another county, but for some reason the towing company still charged us because they said the owner didn't come claim it and they had storage fees.

That's good to hear! Since you followed the proper legal procedures, the expense would definitely qualify as an ordinary and necessary business expense for your rental activity. When you list it on your Schedule E, I recommend noting that proper procedures were followed and that it was necessary to maintain access to the property. While you probably won't need to provide that detail unless audited, it's good documentation to have.

The de minimis safe harbor election does simplify recordkeeping, but you still need to keep receipts! What it really does is allow you to immediately deduct small-cost items (generally under $2,500 per item or invoice) rather than having to capitalize and depreciate them. For example, if you buy a $200 microwave for your rental unit, you can deduct it immediately rather than depreciating it over several years. But you absolutely should keep those receipts - they're your proof if audited. The safe harbor is about how you treat the expenses, not whether you need documentation.

Reporting to BBB does absolutely nothing fyi. They're not a government agency, just a private organization businesses pay to join. Filing a complaint with your state's attorney general office is way more effective.