This business seems very very shady.

Now, other tax incentives like simple business write offs for expenses to set up the properties as an STR that’s most likely still something you can write off against your rental income gains.

I sent you a private message, my apologies, it appears to have been sent twice.

I also use PayPal and Venmo.Some just deposit directly into my business account.I make it as easy as possible for my tenants to pay me.

I have managed my rentals on a very basic spreadsheet (poorly managed) and it is time to clean up my accounting and legal structures.Can anyone opine on a cheap and effective software for the accounting side of the business? 

I've reached general partner status and am growing my syndication business every day. 

Build relationships and don't treat every person as a transaction, and these types of things won't happen to you.We lend to plenty of investors who use the same wholesalers time and time again and don't try to do any of these things because the numbers work for everyone.Build a quality book of business and none of these things will be issues.

https://www.amazon.com/Funny-Decor-Office-Business-Aluminum/...Like this?

Title companies generally won't discuss this matter with general public, but they will speak with an agent because the agent is who brings them business. - You should consider working with an agent that is experienced, so that you don't work alone.

I'm not in the short term rental business but if they are independent contractors then you don't owe them anything.