If it were me, I would approach from two directions.

He signed a contract but the owner never pursued eviction.How should I approach this?

I think the best approach would be going in with a Hard Money loan.

Given the possibility of collecting was very low - I took the same approach as you, throwing good money after bad wasn't worth pursuing, so I sold at a big loss and chalked this one up as a big learning experience. 

Considering our PM agreement, current vacancy & costs I might have to front out of pocket (have already paid the mortgage)How do I even approach this situation?

I’m starting small, with a “Slow and Grow” approach, and have found a 2 BD SFH in my price range (under $150k) that needs rehabbing, BUT it was foreclosed and is now sitting vacant.

House hacking has been my approach here, otherwise the numbers don't really work.

The partnership with Jason Baker exemplified our collaborative approach to real estate success.

At the same time approaching local banks is not bad idea either.

But I completely get it, that moving on is most likely what will end up happening in the end. this isn’t my first election, and was just looking for thoughts to see if other people approach these things different ways, so I appreciate your help today