Hi, Fellow STR investors I occasionally see some hosts to increase nightly rates to a ridiculous number ($1500/night vs. $150/night average nightly rates in the area), and I assume that they are trying to block certain dates on the calendar.

The occasional guy is more like one out of 10 or 15 prospects is a deal for me.

I've had a number of tenants that could have been "my friends" in some other situation, and crazy as it sounds occasionally I'll hear from an old tenant just to say hi.

That is how I occasionally buy houses for one dollar.  

Occasionally he responds to what’s app text message.

I’m cutting the grass, changing the lightbulbs, maintaining the common areas and doing the occasional deep clean in a nice property that they live in.

Thank you, @Cody Lewis You're probably right, I may need a CRM (I've occasionally shopped for them in past).

Worst case scenario I'm looking at 40% vacancy rate and $550/night which is a bit below average and that gives me a Cash on Cash return of 7.7% according to my calculations and a 5 year IRR of around 20% plus a wonderful house to occasionally use for family vacations. 

They have been great tenants for the last 3 years, occasionally they’d be late but would always come up with the rent and tack on a late payment without being asked.

Ideally we would love to keep this as an occasional vacation spot for us to use as well, so bonus points if it is in the mountains or close to water.