Ask an attorney for the cost breakdown, factor in holding costs, assume they'll do more damage on the way out and then ask for a bit more for the headache.But again, especially with no experience with evictions and it sounding like a mess, I would be very tempted to just walk if the tenant is not going to cooperate. 

What is the level of damage?

This way if there’s physical damage by residents the company pays the first $500 to fix it.

Now, I'm imaging a scenario when every one of these tenants move out that I'll be paying their entire security deposit + interest even if there are damages beyond normal wear and tear. 

5 tips i should keep in my mind when buying  rental property? 

I just had tenants move out of my investment property (duplex) without paying for the last month's rent, and the damage they inflicted onto the property exceeds their security deposit amount.

Insurance typically covers only the directly damaged area, not undamaged flooring, even if it's continuous.

I wouldn’t go there myself… you lose a lot of control, your house will see a lot more traffic / damage.  

Central A/C is damaged beyond repair and needed to be replaced, which can't be done economically or with coopperation of the HOA and other neiighboring owners.

Poor communicators, poor housekeeping skills, prescription med abuse, big dogs that they couldn't properly care for, damaging, etc.