We're considering doing something like Dave's cookies via Amazon but that's only semi-fresh baked and subject to shipping damage. 

Ask an attorney for the cost breakdown, factor in holding costs, assume they'll do more damage on the way out and then ask for a bit more for the headache.But again, especially with no experience with evictions and it sounding like a mess, I would be very tempted to just walk if the tenant is not going to cooperate. 

The home was in rough shape—think mold, a hole in the roof, and years of water damage.

Quote from @Alex Tang: One of my rentals was heavily damaged by a fire after Thanksgiving. 

Does the contract include a monetary damages provision?

@Hiyun Park only experienced investors can DIY everything in Class C Midwest areas like Detroit, Cleveland, St Louis, etc.Hopefully the info below will help you:-----------------------------------------------------------------------------------------Recommend you first figure out the property Class you want to invest in, THEN figure out the corresponding location to invest in.Property Class will typically dictate the Class of tenant you get, which greatly IMPACTS rental income stability and property maintenance/damage by tenants.If you apply Class A assumptions to a Class B or C purchase, your expectations won’t be met and it may be a financial disaster.If you buy/renovate a property in Class D area to Class A standards, what quality of tenant will you get?

If you tell the constable that you are concerned about damage, they may talk to him about leaving responsibly.If you are concerned about violence, have a means of defending yourself and let him know it.

While I am still having significant responsiveness issues, the quality of the listing and this new PM’s understanding of market rates is significantly better than my previous PM.I’ll note that during this time, there had been 2 hurricanes in surrounding markets (fortunately no damage to my property from either) that likely contributed to some of this vacancy.

@Logan Lambert well my section 8 tenants that are currently in there are living pretty thugged out and I’m sure that when I need to recover the unit that it’s going to be significantly damaged due to the fact that I had an inspection done three months ago and wasn’t happy with the pictures I received.

Also think about what can be damaged (tenants generally don't take care of the place as well as you would).