By "winning" the eviction, you were awarded a judgment and possession of the property.

You're asking for trouble if you turn over possession with them already owing you money. 

Hello All,I'm new to biggerpockets and to real estate in general, so the only knowledge and experience i possess is purely academic and from conversations (and biggerpockets of course).

The judge will always award the possession order for non-payment here in chicago but getting them out after the possession order is what takes the most time.

Airbnb has a large insurance policy but I don't think it covers artwork so if you have any expensive art that is something to consider.

It may depend on whether it is vacant or occupied, whether you or and agent can get inside to verify the condition, whether you have legal possession or not etc. 

Any adverse possession claim would include the paying of property taxes as wellObviously we have no idea of the terms of your deal but maybe you could wholesale it to the pimp for a few $$

Any advice would be greatly appreciated.426.530 Right of redemption -- Manner of redeeming -- Purchaser to receive writ of possession and deed. (1) If real property sold in pursuance of a judgment or order of a court, other than an execution, does not bring two-thirds (2/3) of its appraised value, the defendant and his or her representatives may redeem it within six (6) months from the day of sale, by paying the original purchase money and ten percent (10%) per annum interest thereon, and any reasonable costs incurred by the purchaser after the sale for maintenance or repair of the property, including but not limited to utility expenses, insurance, association fees, taxes, and the costs to conform the property to the minimum standards of local nuisance code provisions and other local ordinances as authorized in KRS 65.8801 to 65.8839. (2) The defendant shall pay the redemption money to the clerk of the court in which the judgment was rendered or the order of sale was made.

Both were about $1500 and took about 3 weeks (post 3-day) to get possession depending what day you start. 

I would start by researching there. technically, any possessions would be transferred to the estate/next of kin. to be on the safe side, you can request the family sign something saying they are abandoning all property left behind, including security deposit. as always, make sure you comply with local laws. once it is considered abondonded property and you take possession, you should eb free to sell anything you want to recover your damages.