I understand this is my responsibility and I filed an insurance claim and the garage is currently being rebuilt as the entire thing was destroyed.

The Go-Giver: - “Your true worth is determined by how much more you give in value, than you take in payment”The Voice of Knowledge: - “It’s not important to be right, or make others wrong.

I wouldn't worry too much about it, if you have a competent CPA or bookkeeper they should be able to review your books and within minutes have a strong grasp on who gets a 1099 (spoiler alert, not every contractor gets one, I'll be annoyed if I get one since I'm structured as an S corporation) and the amounts to report.1099 filings are usually a loss leader for us, so if you're working with a professional make sure you take advantage of them filing everything for you.

Quote from @Xavien Rafael: Year 1: Building the FoundationThis year is all about setting up your structure, building your business credit, and laying the groundwork for funding and scaling.1.Open Your LLC:•File your first LLC and elect to file as an S-Corp (if applicable to your tax situation).

I did not read the rules around security deposits. you may be allowed to use those funds and still file a small claims action for any remainder, but I can't imagine that it would be worth it if you have at least one month's rent in security deposit. 

There are also additional costs of operating and maintaining an LLC, like separate bank accounts, annual report filings, tax filings, etc.2.

But this year, his team is saying I need to file 1099s. 

Under the Corporate Transparency Act, LLC's are required to file a Beneficial Ownership Information (BOI) Report. 

This should be on file, but not in lease.Tenant interviews should be a part of all due diligence when buying with tenants in place.  

A little late to the gratitude fest, but like @Kerry Baird above, I am genuinely grateful for the old timers here and the new voices as the collective wisdom of this group is something I tap into regularly.