Any insights would be appreciated.https://www.adamssheriff.org/sites/default/files/2018-03/evi...

We've found it has superior reporting features, integration features, and is overall more efficient to work within than other REI-specific software.The downside is QBO is not set up for REI so you'll need to do that or work with an expert to ensure it is set up for your business appropriately.Something else to keep in mind is your entity structure and how your entities file tax returns.

I have file a suit for back rent. 

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.  

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.

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. 

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.

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.