@Russ Draper No reason to believe that the tenant will damage the house, except that he has no intention of leaving. Tenant may get vengeful, though, if a notice of eviction gets posted without him having been given any other (recent) alternatives. No liens on property, investor has owned it outright since April 2017. So you take the risk of Tenant tearing the place up out of vengeance and get him out ASAP via eviction?
@Will G. Are you saying that you'd offer $2,500 "cash for keys" if the meeting went well? Tenant hasn't made any of his rent payments for the past six months, I wouldn't suspect that he'd start paying in full on time just because a new owner was in place.
@Cara Lonsdale Great question! I don't know if there's a paper lease in place, but that would certainly help with the eviction. The squatter would still have to be evicted (given notice of eviction, then my attorney goes to court, then Tenant has 30 days to get out before the sheriff shows up). Also a good point about the insurance.
@Adam Curry So you wouldn't pay any more than $500? Why not? Also, if I were going the cash-for-keys route, it would include a signed document stating that tenancy would be terminated by an effective date with the Tenant and all of his stuff moved out by that date, which would be when I paid him.
Thanks for the answers y'all! Unfortunately the deal fell through before I really had a chance at it (intermediary waited too long to bring it to me, investor found another buyer), but this deal still felt like a good mental exercise so I wanted to share it with the BP community.