He's willing to pay first and last month rent as well as a damage deposit equal to a months rent up front.

It is tough to give up money to a bad tenant, but often times, you'll end up spending less doing that, then dealing with the damage they may cause in retaliation.Good luck!

What are some ideas that can help encourage the tenant to leave the place in good shape and to prevent or minimize damage done by a disgruntled tenant who is getting evicted?

From what I've experienced and observed, water is the biggest source of damage to a home.

In basic accounting, finance, economics and RE, all you need to do is add, subtract, multiple and divide, there is no real brain damage in math.

It is like a dress code in a resturant.

I am always dressed for some type type of labor, even when showing my properties, because I am a do it all yourselfer type and there is always something that needs to be done around my rentals from lawn mowing to painting etc.   

Then she left $2000 worth of damage & cleanup. 

Based on what I know, if the damage is done, its done.  

While out, I found a house with fire damage and made note of the address.