I could probably make it work no matter which route I went; I just am held back by the understanding that once I spend money, I won't be able to spend money again for a good while (buy and hold), or even worse take a haircut because I don't want to be in a situation that I got myself into. 

Traditionally, DSCR loans that allowed STR have always wanted DSCR to be calculated on long term rental rates OR 12 months of actual performance or some heavily hair cutted version of Air DNA and all of these products would price gauge on rate.

They are never the cheapest, but if you hire the cheapest you get to follow them around and add a job of micromanaging to your list of daily activities.CEO's of multi million dollar companies golf 3 times a week, shop for cars mid day, get suits tailored, hop a jet to fly fish, have perfect haircuts every week, volunteer at a shelter passing out food, get photo ops and make company motivational videos.

Realistically you're probably taking a haircut on these purchases, and definitely continuing to lose money every month if you keep them.

Moving forward blindly on that deal would have put our investors money at risk, which isn't an option, so WE took a $60k haircut to prevent that.

I wonder what the “this can’t go on forever” crowd would say if you asked them if they thought haircut prices would keep going up forever?

In most cases, the borrower would file BK and unsecured creditors would largely be wiped out or take a serious haircut.

Needs much more a haircut first.

In joshua tree and phoenix area there are lot of STR haircut today , if the vision is for 30 years it could be a good deal.

Haircuts are the third building to the left.https://www.youtube.com/watch?