If the underwriting goes smooth and I can have the cash on hand at closing, then maybe the owner wouldn’t care how the cash offer is funded. 

In that case, you'll strongly want to consider what putting personal-use property inside of an otherwise business-use LLC would do to the liability shield, as well as insurance and tax reporting.There are several considerations that can go into the analysis of whether you need an LLC or whether a large insurance policy will suffice.

But for judgements liens and all that who cares they are snuffed out at the sale.

I can give you dozens of examples of owners who believed they could care for their property better than a stranger.

Quote from @Steve Hiltabiddle: Hey Lenders,  I'm going through my first default process on a private loan for an investment property and I've done so with the assistance of an Attorney. 

If any place has HOA/POA I would be very careful with those restrictions and talk to plenty of people including every board member before buying about their views on STR. 

Reading those little books that guests and sign and comment in can be very helpful and grounding when you have those times when it seems like guests don't care.

Otherwise contract a service for the season that will automatically take care of for every snowfall.4) YES you need to heat them!

Be careful, these landlords are notorious for not paying 

The resident takes care of everything and usually stays 3-5 years at least.