You can’t allow these folks to destroy your property and let it go to crap 

The outside looked decent (other than a couple broken windows and hole in the roof) but the inside was destroyed right down and including studs and rafters/trusses.

Personally for me my relations with my bud matter more than the money and I won't like to destroy personal relations at monetary cost.

Imagine you take out a 30 year loan for 150k on a duplex and a tenant destroys your property.

The delay in reporting the incident to both me and authorities pretty much destroyed any chance of finding the person responsible.

Your first line of the post states, "I'm obviously going to have my own emotions attached to the decision"  so my question to you is, how would you feel if a tenant you're renting to destroys the house? 

Prior to a car running into their building and destroying their home they did have 3 dogs. 

in my limited experience over the years these are full on hoarders and if the person lets this go this house will be loaded with crap within a year and basically destroyed on the inside.. 

If you stay on top of it with fogging and spraying, you have a good chance of destroying a small breeding population.

I would have the goal of outsourcing it once you've got some traction but things like list fees and shipping can destroy that budget.