Work out a deal that way.

The only disadvantage would be that you would most likely not be able to get financing for this property, but if you have the cash to invest, it should work out very well for you. 

Paying me for wood and gutter work out of that money is actually paying me with my own money that I already had.

I am not expecting things to work out as you implied but prepare a good exit plan.

Get a written agreement from the neighbor that they'll allow it to stay but it must be moved onto your property if it is every replaced.Talk to the neighbor and see what you can work out.

Ultimately STR here may not work out but we do have a desire to buy in the area.  

You can't just HOPE it will work out - you have to run the numbers.You have to make sure your numbers are realistic.

You can find the deal and work out an agreement with the experienced investor.

@Alex GarridoInvesting in Panama City would work out for short term rentals because you could pay for the holding costs and maybe profit nicely while hopefully the value of your property increases over the long term.Unfortunately, it’s illegal to rent for less than 45 days and personally I’d never suggest anybody gets into an illegal business overseas.I’ve come across a couple rare buildings in Costa del Este who have a permit but, as you could expect, it’s reflected in the price.

I would speak to local banks and credit unions since this is where you might be able to work out a win-win financing solution.