Wait what?? I had no idea about these state filings. I'm in Michigan - do you know what might be required here? Is this something completely separate from the tax extension stuff?

Michigan requires an Annual Statement for LLCs, due February 15th each year, and there's a $25 filing fee. This is completely separate from your tax extension - it's more about keeping your business registration active with the state. You file it with Michigan's Department of Licensing and Regulatory Affairs (LARA), not with the tax authorities. The good news is that Michigan sends reminder notices, but don't rely solely on those. Missing the filing can result in your LLC being not in "good standing" which could affect your liability protection. You can file it online through Michigan's LARA website. This is definitely something to add to your annual business compliance calendar!

30% seems high though? Doesn't it depend on your profit margins and tax bracket? I've been setting aside about 20% and it's been enough so far for my freelance work.

This is really helpful advice that I hadn't thought about. With my parents' history of financial abuse, I definitely need this extra protection. Is this something I should do before or after catching up on my back taxes?

I would recommend doing it as soon as possible, independent of catching up on your back taxes. You can request an Identity Protection PIN directly from the IRS website by going to their "Get an IP PIN" tool. This will help secure your tax account immediately, even while you're working on filing your past returns. The IP PIN is valid for one calendar year, so you'll get a new one each year. This ensures that even if someone has your personal information, they cannot file a fraudulent tax return in your name because they won't have the current PIN. Given your history of family identity issues, this extra protection is definitely worth setting up right away.

The Fresh Start program is great but it's mostly for people who've already filed and owe money they can't pay. For unfiled returns, you need to file first, then look into payment options like an Installment Agreement or Offer in Compromise depending on your situation.

Thanks for that warning. My goal isn't to change careers - I'm planning to expand my real estate portfolio and possibly move into commercial properties in the future. Would that still count as my "current" business or would the IRS see commercial real estate as a new trade?

Expanding from residential to commercial real estate would generally still be considered the same trade or business since you're still in property management and real estate investment. The IRS would likely view this as a natural progression within your current business rather than entering a new field entirely. Going from real estate into something completely different like investment banking (as in my case) is what triggers the "new trade or business" limitation. Just make sure you document your intention to expand within real estate rather than presenting it as preparation for a career change.

In TurboTax, you'd enter it under the Schedule E section for your rental property. When you get to the expenses part for each property, there's an "Other Expenses" category where you can add custom expense items. That's where I put my real estate continuing education costs last year.

Does this also work with retirement account withholding? I take distributions from my IRA and could potentially increase the withholding there instead of making estimated payments.

Yes, it absolutely works with retirement account withholding too! Any federal income tax withholding (from W-2 wages, retirement distributions, etc.) is treated as if it occurred evenly throughout the year, regardless of when it actually happened. So increasing your IRA distribution withholding late in the year is a perfectly valid strategy to make up for estimated payment shortfalls. It's especially useful if you realize in November or December that you're going to owe more than expected.

Thank you for clarifying this! I was looking at the wrong line on my previous return. Looks like I need to pay about $2,400 more than I thought to hit the safe harbor. Better to know now than get hit with penalties later!

Wait, can employers actually do that? I assumed once the year was over, all the tax stuff was set in stone. Can they really go back and fix withholding errors after the fact?

They can't change the actual withholding after the year ends, but there are a couple of options. First, they can issue a corrected W-2 if there were actual errors in reporting. More practically though, some employers will provide compensation to cover tax liabilities resulting from their payroll errors - basically paying you an additional amount to offset some of your tax burden. This isn't required by law, but many companies have policies for this since payroll errors can cause significant financial hardship for employees. It's worth having a conversation with both HR and payroll about their error resolution policies. Document everything, be polite but firm that this was their error, and ask what they can do to help make it right.

Exactly this! The IRS calls it a "Waiver of Penalty Due to Federally Declared Disaster, Mathematical or Clerical Error by the IRS, or Certain Other Conditions" (Part II of Form 2210). A payroll system error could qualify under certain conditions!