If he agrees and was a very long term tenant I would be reasonable lenient on what I charge him for....pretty broad on reasonable wear and tear, but if he F'd up the place with his own crap work I never authorized or trashed it beyond reasonable, then I would deduct as indicatedBefore I would fully commit to any plan of "he was there 10 years and was a good tenant, just give him his full deposit back" I would need to really see what the property is like........ if its decent, I would happily aggress to that..... but until then, don't stop the eviction processKeep going on the eviction and don't accept a dime of $$.....

What happens if the tenant is a crap bag?

Typical Miami crap. 

Oh, I only smoke outside" bull crap!  

absolutely amazing so even when yuh win the ejectment they give them 10 days to get outWhat a crap law 

You don't need this crap.

When the crap hits the fan, pooling of money for deals will absolutely function like a pyramid scheme for some unscrupulous operators...they will rob from Peter to pay Paul, many times without bad intentions.It also takes good internal record keeping to keep from commingling funds.

The driver could change his mind; he could crap out after a month; etc.

In other words, a piece of crap in the worst area rents for about the same as a solid property in a good area. 

And as previously suggested, get as detailed a SoW as you can, so everyone’s on the same page and don’t take any crap like I did. ;) But after all is said and done,I’d do it again.