The biggest issue I see is that they are looking to restrict STRs in the area so why would I buy there knowing it could all go away.

The biggest issue is that forgetting to assign a location or choosing the wrong one can mess up your balance sheet, leading to inaccuracies.

And no matter what, keep an eye on how your financing structure lines up with your exit strategy.Where do you see the biggest risk.. sinking money into improvements or letting the buy back linger too long?

My intent was to move within a year and rent it out, but we have been having unforeseen expensive issues that I am looking to get advice on.1) HVAC: Our biggest issue.

I would like to buy a multi-family and convert into micro units to maximize revenue.

In the peak season the math is better.We started charging MTR a bit more for the four biggest holiday weekends of the year. 

The beach has taken about a year and the jungle house will take about 4-5 years because we are paying off some seller financing with the revenue from the short term rentals.I would say that I can definitely make more money investing in real estate in the United States than in Costa Rica.

There's no $$$$ in teaching you how to implement the action items I shared above which is why the higher revenue generating systems are sold, usually to real estate investors who don't know any better. 

I like option 2 to diversify the investments in 3 smaller rental propertires, 3/2 around 1500 sqft, in good school districts which will open the biggest pool of tenants. 

The biggest 'danger' I've experienced in the coaching space was coaches who took the cash and wanted me to follow 'their' program rather than coaching me where I am to get where I wanted to go.