If you're running a short term rental, you might consider using a manager that will take care of cleaning as well as bookings etc. 

I was thinking they could take care of things like research options for insurance, find contractors for repairs on rentals, intake tenant maintenance requests, assist with finding deals, and organize the documentation for each property.

I tried tenant gardens on my house hack and it cost me (tenants leaving water on, attracting wild animals, wasn't taken care of, list goes on)Lastly, what is your plan for funding?

Palm Harbor, and oldsmar west to New Port Richey are stable but you have to be careful street by street where you're investing.  

Do your homework – ask folks, read reviews, and compare.

Yea I always let the guest know I will send someone over to take care of it right away.  

At the end of the day, you want to feel safe and secure they manage your property first, and that your tenants are well taken care of too.

The new lender wouldn't care what the current loan is, as long as it's paid off.

You should pay for anything that you care about and want to be maintained. 

You will have to be careful though, to target a refinance after 2 years to free up your VA eligibility to re-use.