Seems like there is a bit of Dave Rambsy elements in there that need to move away from but here is a course of action:1.

Pushes the cost of damage protection insurance onto the hosts and guests.

I have a Google Sheet that I'm using to track different elements of the project but I'm wondering if folks have success using other software that they can share with me?

It's not common, it's inevitable.  14 years without a tenant purposely damaging a unit (knock on wood).

They pay the rent on time, every time, don't damage the house and don't cause any problems.

And then trying to convince the masses that there is no competition on the MLS.. for Pete's sake, that alone should make people run away yelling "scam".On the MLS, you are competing with real estate agents, that buy houses themselves on the MLS, you are competing with the traditional buyer, you are competing with other investors crazy enough to try to look for deals on the MLS (yes there are plenty), You are competing with agents that look for deals for their list of cash buyers.Every single element of this entire thing is just retarded. 

None of the other planks are cupped or show signs of water damage. 

Like many others on BP , I do prefer some element of privacy as I do not want tenants and such googling me and finding threads where I have used them as an example .  

It's how those companies handle the damages that's different.

Be sure to spell out in your leases if you do go this route who is responsible for repairs to this type of damage.