Collecting for damage from a holdover tenant

[Roy Coons]

Hello,

We purchased a 4-plex in June and all units are occupied. One tenant was on a month to month and the place was filthy and smelled and in dire need of work. We have a PM so we asked them to request the tenant move out, they are scheduled to vacate at the end of September. The tenant has been in the unit since Nov. 2012 and there is a lot of damage. At least 5 interior doors have holes, drywall is marred and dented in places, some trim removed and broken, closet doors broken along with broken light fixtures etc. 

My question is this, since the tenant only had a $300 damage deposit how aggressively should we pursue this tenant to recoup some of the cost of repairing the damage? This family clearly has little to no money as they were struggling to pay the rent ($800 a month) so I think it is a waste of time to go after them but my wife wants to "stick it to them".  They are allowing the contractors in to make quotes so at least they are cooperating in that regard.

Thanks for the advice

Roy