Not dealing with bad tenants (letting them pay late, do damage, etc.)Understand that vacancy is better than having a bad tenant.

I filed a claim and my insurance company is estimating the damage currently.

And unless they're damaging the unit, I don't think I would go so far as to evict them for not paying the deposit, it will end up costing you more.What you might be able to do (check with an attorney) is charge them a late fee for not paying the deposit.

in the last picture with the white PVC drain lines, the floor joists don't look too great but its always hard to tell in pics but there could be some rot or pest damage there. 

If not, this is going to add stress to your marriage and your relationship to your children, and typically significantly more than most people expect.Your house is inevitably going to be damaged and changed during the time that it's a rental.

Is there a third-party company that offers Damage Protection coverage for midterm rentals?

This is the “free answer” from Google, so it’s worth what you paid for it…https://www.justanswer.com/law/80qys-live-arkansas-neighbor-....Lawyer: LawEducatorUnder the common law of property you are entitled to trim branches from any trees that are overhanging on your property but must do so by exercising reasonable care not to damage or harm the tree.

We know there are other STR owners blocks away from us and theirs opportunity to meet them as well as other business owners?

Even personally holding the discussions with the tenants potentially damages YOUR outcome.Landlord Representation in SF

We figure we'll have to replace them every 3-5 years as the saltwater damages them beyond use.Gas: Weber 2-burner (It was less than $300 delivered in early 2022) -  https://www.amazon.com/gp/product/B01HID4Y7Q/Charcoal: (May not be this exact one, but it's similar)  https://www.amazon.com/Weber-741001-Original-22-Inch-Charcoa...Honestly, I don't know how much guests actually use them.