Tax Implications for Pop Up Retail Store Business - Do I Issue 1099-MISC for Mall Rental Payments?

What if the mall is owned by a corporation? I thought you didn't need to send 1099s to corporations, just individuals and LLCs?

You're asking a good question - you're right that payments to C-corporations are generally exempt from 1099-MISC reporting requirements. If the mall or property management company is a C-corporation, you wouldn't need to issue a 1099-MISC for the rental payments. That's exactly why it's important to collect the W-9 form - it will tell you the business entity type. If box 3 is checked indicating they're a C-corporation, then you don't need to issue the 1099. But if they're set up as an LLC, partnership, S-corporation, or individual, you would still need to issue the 1099-MISC for payments over $600.

Does it work for other business expense documentation too? I have a bunch of contractors I work with and never know who needs 1099s.

I'm skeptical about AI tools for tax stuff. How accurate is it really? Does it actually know all the tax code nuances for different business situations?

Yes, it absolutely works for other types of business expense documentation too. I uploaded all my contractor payments and it sorted through which ones needed 1099s based on payment amounts and business types. It even flagged a couple contractors I would have missed. As for accuracy, I was skeptical too at first. But it's specifically designed to know all the tax code nuances - that's its whole purpose. It's trained on the tax code and regulations, so it catches details and exceptions I would have missed. My accountant actually verified its recommendations and was impressed with how accurate it was.

Wait this actually works? How does it get you through when the normal IRS line keeps hanging up?

Sounds like a scam tbh. Why would you need to pay a service to call the IRS? Can't you just call them directly and wait on hold?

Yes, it actually works! It uses some kind of technology that navigates the IRS phone system and holds your place in line. Then when it reaches an agent, it calls you and connects you. So instead of spending hours on hold, you just get a call when an agent is available. You definitely can call directly if you want, but the problem is the IRS phone lines are so overwhelmed that most calls get disconnected before you even get into the queue. Last year I tried calling directly for three days and kept getting the "call back later" message. With Claimyr I was speaking to an agent in about 15 minutes.

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.