There were issues syncing the reservation calendar, and it is nearly impossible to reach a customer support representative with Booking.com as an individual STR owner.

I'd go for the best location, ideally, but without a strong compromise on your funds.

I dont like the ideal of prospecting 5 days a week and im a single dad so the weekends are a no-go. 4 days for calling 3 days for follow up and appointments. 

As for insurance I deal a lot with that here in Tahoe and western Reno.

Many companies will be lazy/cut costs after they have a large enough customer base.Currently Dataskip.io is the best. 

.- I do believe having multiple backups is ideal.

The question comes with various customized details but it's the same answer over-n-over again, to such a degree that answer-burn becomes a very real thing. 

As a bulk-delivery service, we have to protect the deliverability of all our customers.

IDEALLY, we would like to find a property that has or is capable of being converted into a “mother in law”, “ADU”, “Casita”, or any other separate living quarters in which we could rent out the main portion to a tenant (short term or long term) and then use the separate space as our own for when we come and go with business.

Ideally, that's what I would like to get into developing 8 - 16 unit complexes that can fit on a smaller footprint.