Since in Florida there's only one major insurance which is run by the state it's called Citizens they require an inspection in order to determine if they will insure you or not.And yes if the inspector gives your roof no life left this they will not insure you.

It's got a bunch of tips and checklists on how to get an MTR up and running. 

You need to run accurate, complete, numbers first.

I run an air BnB out of my home in Southern Vt And I own 2 condos at Mt Snow. 

So when I was asked to put a penalty in the contract for running past the completion deadline, I would always counter with "okay fine, then let's put an equal amount of reward in there if I finish early, okay?" 

It will be best to choose one and run with it for a bit so you have a base of comparison for the future - keycheck is a solid start.

To me, monthly cash flow is better in the long run.

The issue I'm running into with this is the area I'm planning on moving to isn't exactly the most affordable, and so even with 0% down, you still have to make the mortgage payments, and you're only qualified for up to an amount supportable by your in-place income, which of course makes sense.

I'd be happy to run some numbers for you!

I would run a cost estimate if you haven't.