A tenant can do $20k of damage pretty quickly and skip town never to be found again, if you aren't careful.  

Have them blown out and truly winterized by a reputable company.

If you're solely looking to invest passively longer-term you're probably better off finding a reputable syndicator and investing passively. 

They did not make an offer to pay rent/damages/legal fees before the deadline of the eviction. 

I’m worried they won’t leave or damage the property.

Yes, most of the reputable lenders have a min loan amount of 65k - 75k with a minimum of 40k - 50k of that amount going toward the purchase.I've been down this road before with a few investors who want to buy cheaper homes and what I can tell you is that - 1) It's not easy and 2) You WILL NOT like the rates, fees, and points.Think about it, what does a lender stand to make on an interest only loan for about 40k. 

But that means we have to push this out even further and the longer the issue isn't addressed, the more damage that is being done.

Did it sustain damage?

Not sure of their reputation, any insight or tips for navigating this process at all are apricated.  

Any advice on how to source reputable contractors in a specific area?