Most smart systems like these have simple apps to use to set these routines up.

He can do routine drive by's weekly to check on house.

Just give the guest a disclaimer that due to cleaning routines, the hot tub may not be at max temperature the first night of their stay.

It all comes down to the HOA, how it is managed, and their financials--especially look at the reserve analysis and the balance sheet (it is public record, so call up the manager and ask for it before making an offer--it should be part of your inspection routine with HOA's and COA's).  

I routinely do two year leases as a minimum.

Some predatory travel nurse agencies routinely cut pay as soon as the travel nurse begins their assignment with a take it or leave it approach knowing the nurse waited weeks without work for the contract to start, gave up other opportunities, and accrued thousands in out of pocket expenses for flights, rental car, signed a MTR lease, and maybe even relocated their family.  

They're a great company that work with local licensed realtors to perform showings as well as routine inspections if needed.

I routinely check Craigslist, but didn’t think to check Facebook Marketplace or joining any local STR groups.

.  **** breaks routinely.

Additionally, I happen to be doing a routine walkthrough of the property tomorrow.