Can you explain more about the S-Corp thing? I'm in a similar situation to OP and keep hearing about S-Corps but don't really understand the benefit.

Sure! With an S-Corp, you pay yourself a "reasonable salary" that's subject to self-employment tax (the 15.3% for Social Security and Medicare). Then you can take the rest of your profit as distributions, which aren't subject to self-employment tax. For example, if your business makes $105k, you might pay yourself a salary of $65k (which would be subject to self-employment tax) and take $40k as distributions (which would only be subject to income tax, not self-employment tax). This could save you about $6,120 in self-employment taxes (15.3% of $40k). The key is that your salary must be "reasonable" for your industry and role - you can't just pay yourself $20k and take $85k as distributions. There are also additional costs like increased accounting fees and payroll processing. Generally makes sense once you're earning over $80-100k consistently.

But doesn't the QBI deduction phase out at higher income levels? Im not sure OP would qualify with $105k income.

Really? I thought Free File was only for super simple returns. Can it handle things like stock sales and early retirement distributions? I'm not confident in doing all those calculations myself.

Free File through partner companies (like TurboTax, H&R Block, etc.) can absolutely handle stock sales and retirement distributions if you qualify by income. The software is the same as their paid versions, just offered free through the IRS partnership. If you use Free File Fillable Forms (the direct IRS option), it's basically just electronic versions of paper forms with basic calculations. That option requires more tax knowledge since you need to know which forms to fill out, but it's still free and available to everyone regardless of income. For your situation, I'd recommend using one of the Free File partner software options to file your extension now. Then when you return, you can use the same service to complete your full return with all your investment documents. Much better than paying hundreds to a storefront preparer!

I second this. The IRS is much more accommodating than people expect when you're upfront about your situation. I've been on payment plans twice and it was simple to set up. The interest rates are usually better than credit cards too.

Thanks for bringing this up - good point! How do I verify I'm getting the W-9 from the actual property owner? The lease agreement I sign is always with the mall management company.

The lease agreement can be tricky because sometimes the management company is authorized to sign on behalf of the property owner. You should specifically ask "Who is the legal owner of this property that will be reporting the rental income for tax purposes?" That question usually clarifies things. The W-9 itself will also tell you - look at the name and tax ID. If it's a different entity than what's on your lease, ask for clarification. Sometimes the management company will provide a letter explaining the relationship between the entities if they're affiliated.

Yes, you would aggregate payments to the same legal entity. So if Mall A and Mall B are both owned by XYZ Properties Inc., you'd add up all payments to XYZ when determining if you've exceeded $600. That's why getting those W-9s is so important - to identify when different locations have the same ultimate payee.

That makes sense, thanks for the clarification! Guess I need to start tracking these payments by parent company instead of just by location.

That's actually a really helpful suggestion! I hadn't thought about switching providers, but it makes sense to look for better investment options. Did you have any fees when you moved your Roth IRA to Fidelity? And how long did the whole process take?

No fees to transfer the Roth IRA to Fidelity - most major brokerages don't charge for incoming transfers. The whole process took about 2 weeks from starting the paperwork to having everything settled in the new account. Fidelity handled most of the transfer work once I filled out their forms. The good part was getting access to their research tools and fund options. I met with one of their advisors (free consultation) who suggested a portfolio mix based on my retirement timeline that's been working well.

This is a really important point! I had a similar situation happen and it's easy to focus on the loss and forget that the money you put in is still accessible if needed.

Did you have any issues with penalties even though you were owed refunds? And how long did the whole process take from when you first contacted the CPA to getting everything resolved?

No penalties at all since I was due refunds! That's the good news about being owed money - the IRS doesn't penalize you for filing late when they owe YOU. They only charge penalties and interest when YOU owe THEM. The process took about 3 weeks total. First meeting was dropping off all my documents (W-2s, 1099s, etc.). About 10 days later they had all the returns prepared for me to review and sign. Filed electronically for the two most recent years, paper filed the older ones. Got my electronic refunds about 3 weeks after filing, and the paper filed ones took about 4 months. The whole thing was way less painful than the years I spent worrying about it!

This is so true! Those places prey on fear with their scary commercials about IRS collections. A regular tax preparer or CPA is totally sufficient for unfiled returns when you have all your documents.

Thank you for this warning! I've been hearing those commercials and they definitely play up the fear factor. I'll look for a local CPA instead of one of those national chains. Appreciate the advice!