Could you agree to do 5 houses, staying 2 years in each (which would be better for your capital gains taxes)? 

I have just moved into a new city (New Orleans) and want to get into the STR space through co-hosting and really become an expert in the process, what's the best way to gain exposure, connect, contact and gain clients in a new area. 

B sells the property in 2004, realizing a gain of $21,000.

I flipped a property several years ago and ended up dumping my gains into an upgraded primary residence.

Usually the first few years you’ll get a paper loss, so no taxes to pay, but once you show a gain you’ll have to pay.

Would you build a portfolio with long term rentals prior to investing in short term rentals, or would you use short term rental opportunities for quicker profit gain to expand on purchases of long term rentals.

Note that there is a 5% capital gains tax in Panama and you'd also have to pay capital gains taxes in the United States.

That can hurt ROI as well.Mexican Peso has gained about 10% this year against $ so maybe there is opportunity there.How is ROI in Colombia, especially in the big 3 cities?   

I am excited to get started and hopefully gain confidence to pull the trigger on an investment property. 

The only thing that you have said that makes me question the PM outright was the lack of a key for the sheriff to gain entry.