Any recommendations on contractors with investing experience / mindset and a property management company that returns your calls? 

In our initial underwriting process we always call around to the various comps to compare vacancies and rental prices on the various unit sizes. 

Remember to call the tax collector's office (back taxes) and health department (if there's a septic system).Find an agent who's willing to working with flippers and investors.

Picture a problem on a nice winter Saturday with the wind chill -17 and you’re getting an emergency call at 2am.

Have your tenants initiate the call...

I ran into the same issue locally (SoCal) where you get these inexperienced investors (I call them idiots, but that's semantics lol) that watch HGTV and think they can flip homes. 

A recent example is that I called a broker (not the main one that my partner uses) to ask about recent sales and what he's seeing in certain areas of a city.

Call some of the 500 bandit signs you see all over the roads.

IF (big IF) you do get a letter or call from an attorney, let them know the bill is owed by the tenant, and if pushed, you intend to counter sue for excessive damages and report the drug paraphernalia/evidence of use to the local drug enforcement agency.We are talking about a small-claims court issue at best, and personally (I am not an attorney) I would keep all timelines, damages, photos, expenses and communications in a file. 

A recent example is that I called a broker (not the main one that my partner uses) to ask about recent sales and what he's seeing in certain areas of a city.