Sounds like there might be some "upside" as future development takes place with increased demand, but it's important to know the financial situation up until that time period.

.: I paid cash for 5 small condos over an 18 year period.

The cash value of the policy also earns a dividend during that same period, so assuming that is 6%, your cash value grows by $5100.

Local STR laws can change within a relatively short time period, and you want to have a backup plan for if/when those changes take place.All the best!

In the end, I prefer the long-term rental route with a good tenant though and over time when I start traveling for extended periods again, I will likely shift them back to long-term.I personally, would not purchase a property for the sole purpose of being a vacation rental - it's just not part of my investment strategy though, I have met people who do quite well with that model. 

I have worked with plenty of PM's during their tenant turnover period so no I do not get the picture.

From a mark to market perspective these houses have been some of the best investments % wise in the 8 to 16 month investment period I've been in REI.

They are out to pray on those who sign up for their service during the trial period, so that they can process a payment on your credit card.

The 30-year fixed portfolio loan with an intro 10-year IO period has been popular for clients of ours!

Then when you sell you will get to prorate the gain between tax free (the period you lived in it) and taxable (the period it was a rental)4.