We talked to some people (banker, pm, etc) about a weekly rental property but seems it would make more sense if you wanted to use the place yourself and not too concerned with making money.

This has caused much confusion to many people over the years

Unlike when walking a dog, they aren't present to see it happen or where so that is a common and practical approach to handling the issue for most people.

But the same argument people use for self managing, (nobody will care as much about your property as you.) is definitely true of your accounting. 

When people mean by bringing cash to the closing is that you must have funds to close -- whether they be from your own pocket or someone else's pocket.

People like walk out basements, trees, water, boulders, views or lack of view.  

(Zillow data) I've been doing open houses for an hour twice a month, and have had 4 applications so far from people who went. 

I know many people that have been unable to rebuild after the 2020 California August lightning fires because they were only insured for about 1/2 or less of the actual replacement value.

I’m doing some digging and am aware of people who have used Traveler’s Insurance and USAA. 

I have a contact that may be able to get you connected with the right people.