So consider how much asset protection means to you and be willing to potentially pay more because you'll have less lending options available to you, the more complicated you make your entity structure.Hope this helps.

What options do I have?

You could give them the option to re-up the lease with the $50 increase and lock the rate in for a year or go month-to-month at market value which would be a $200 increase.

But tax purposes, just getting a mortgage on your primary is probably still going to be the best option. 

That way you only have to come out of pocket 3.5% to 5% depending on if you use FHA or Fannie Mae.If you decide to buy an investment you will need 15% down and buying out of state is an option but there are other great counties in Florida.

If you do, you could give them an option for a month to month lease if they use you to purchase their new home.If that is not an option, I would stick to the lease end date of June 30th.

Assuming you are keeping fairly apprised of debt options and interest rates, if the T12, cap rate is less than your interest rate, I would personally move on (exceptions apply if rents are several hundred behind market rates)These are three quick ones that shouldn't take more than 10, maybe 20 minutes to quickly determine and you don't even need a simple or complex excel model to complete.  

If I do go the property management route - can i get a limited service option (say in which I find the tenant, collect rent, handle most maitnenance issues) and they primarily are liasoning with my vendors during US business hours and handle any urgent maintenance issues?

Totally a viable option but keep in mind the documentation of the process and making sure that YOUR material participation does not exceed anyone else in the home - for example, your cleaners or maintenance people. 

Option 2: Purchase additional properties and build portfolio I know that there are some tax implications to no having the mortgage payment to consider.