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.

Hey Aaron - just a word to be careful in Orlando area as the area is not performing quite well at the moment due to oversaturation. 

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.  

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.

Consider factors such as the property price and financing, income and expenses, cash flow and return on investment (ROI), market trends and demand, future appreciation and exit strategy, and seek professional guidance.

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. 

If you want to make money off of your site, it's a good idea to either hire and SEO professional or study the field yourself.Mitchell Herman

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