I don't think the fact that prices have gone up 5 years in a row is a good clean indicator that they will continue to do so, if it cashflows today and I can hold it for 20 years inflation should do most of the heavy lifting for me. 

So invest in some kind of real estate like apartments that need heavy lift and get the bonus.Otherwise life settlement partnerships can also give you big deduction year 1. 

In my eyes, "heavy" competition is very subjective.

You’ve already done the heavy lifting, so giving up control might cost you more than you gain.Ask the buyer why they want you to terminate the contracts.

Assume heavy STR and this is what is driving the market? 

For overnight rentals, functionally it is a bedroom.

If you lean on it too heavy, it may just tell you what you want to believe in the first place.  

That's a heavy load to carry over time and sure will come with consequences.

$300K is a lot of credit card debt and probably didn't happen overnight (unless it is medical bills). 

Short-term rentals like Airbnb can perform well in tourist-heavy areas like Vegas, but be sure to check local regulations.