Also, in the right areas in Tampa it seems that a STR could be great, and my fiancé does have enough free time to cover the extra time-commitment a STR would require, that part wouldn’t bother us. 

If its truly intended to be an investment I say look at a different market and use the extra money to rent a sick house for a week or two in Florida. 

You do but guess what, you don't' get that extra $100,000 back.

IF I'm going to make extra principal payments to pay off a "low(er)" interest rate mortgage early (compared to today's rates), my gut reaction would be to pay off the highest interest rate mortgage first.

You'll provide Chinese Hand Fans to the tenants at signing? 

They should be able to assist you with this request and provide any necessary information regarding fees or requirements for adding another person to the booking.

Investment Info:

Single-family residence buy & hold investment.

Purchase price: $800,000

Cash invested: $400,000

Home I rent to a family of five

Something as simple as you providing the materials for the work and/or the tools can classify a person as your employee (state specific).

It sounds like you have a paying tenant where you occasionally make a little extra on with a late fee.

Please provide any assistance.