I have file a suit for back rent. 

Not mentioned, is recognition of other opportunities that a well-secured note may provide strategically, if placed well.

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.

My front is similar with packages delivered most days and being very confident if delivered to the front door that they are very secure.  

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

I'm hoping to broaden my real estate literacy and savvy, as well as learn how to source, evaluate, and secure sponsors and deals that meet my financial goals.

What’s the best way to secure a deal, and not encounter with another wholesaler going after the same property.

If the cost of the couch removal and other items isn't that significant, maybe just pay out of pocket and don't renew them for another term (or take it out of security deposit if you have one).

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

We also were able to get the property taxes reduced by filing a complaint with the county.