I have to manually send each message though and my intention is not to automatically blast people with spam.

Most utility companies have a Landlord program that automatically switches utilities to the landlord once the tenant cancels service.

That worked for the first year, but with the first lease renewals that I did, I moved the automatic payments over to Rentecdirect.   

This was really great for keeping me organized- it allows you to automatically send bills, add payments and also has time sensitive features baked in (for example a late fee applied on day 5).

This is the only one that will do things automatically.

But why is it fair, or expected, for a guest to automatically transfer the financial downside of CV to the homeowner? 

Give notice that leases will not be automatically renewed under the current terms at the end of the current lease.  

If you set up automatic email alerts with your agent, then you can see what kinds of housing are coming onto the market.

Now after setting $200 aside each month for expenses (in FL AirBNB automatically adds my taxes so I don’t have to set aside for that) brings me to an average monthly profit of 2,725.

There's more paperwork and you don't automatically drop PMI once you hit 80% LTV.I don't see any advantage of using a private lender unless you have some unique circumstances.What price range are you considering?