. $20K in reserves isn't a lot if something goes horribly wrong and there are damages if you default and he takes the property back.

If you are trying to piece everything together yourself remotely I think the time and brain damage and extra cost in time and cash you would be better to go yourself and do it. 

This is my first extensively water damaged home that I may purchase.

I'd check for that before installing LVP and replace the subfloor where needed and treat any termite damage. 

But I draw the line when there is risk of damage to the property, annoyance to the neighbors, health concerns, pests, etc.

Really low prices bring dregs and all the work you did could get damaged.

Things to consider: daily internal operations, external branding and operations, lending, in addition to inside out *legal protection and outside in** legal protection, privacy/anonymity/identity protection and security...Prevention measures at different levels, preventing the attack from being initiated vs preventing the attack (lawsuit) being successful vs reducing the damage of a successful attack.... there are many elements and I see people pick one and argue about it without looking at the whole

For example, what if a tenant leaves with significant damage and it takes you $20k and a few months to make the unit rent ready again.

If I was the tenant that got damage from another tenant's water heater, I would expect him to pay the bill.If it was a pipe in the building and not in their unit, then I would think the landlord would be responsible.

This way the tenants will be held responsible for any damages.