It definitely can help add time back into your life and they can be a great source of information on vacancy rates, current market rent rates, etc. 

Sure you can sell it and take that cash and put it into something that you can manage yourself, but with an interest rate as low as you have it for, I would not.

Go to Etsy and search for "rental property tracker," and you will find hundreds of nice spreadsheets to track 10-20 rentals, usually for under $10.Software has extremely helpful features like online payments, marketing syndication (click a button, and your property is advertised on multiple sites), electronic document review/signing, maintenance tracking, and owner reports.

Chances are you'll want to refi in a few years anyway once rates fall.

The seller is paying 20k in mortgage interest, given the current interest rates I would need to 45kish in mortgage interest for the said STR.

Then find out if rules were to ever reverse, do the CC&RR's have a clause protecting existing rental permit owners so they are grandfathered in despite any changes in the future.Also, check the OTA's to see if anyone in this desirable lake location are advertising their 30+ day rental.

There are plenty of lenders that don't require experience to lend, but leverage/rate might be altered a bit.

I keep wondering about insurance, vacancy rates, if tenant selection is a bigger/ different factor, terms of the tenancy and differences in opex and capex?

Do school ratings matter for SFH?

In some markets you won’t get the higher booking rates and occupancy numbers without a pool (Florida and Arizona come to mind).