I send my checkout message at 9:00 reminding them that checkout is 11 and its $45 for a late checkout at 1:00 They either leave on time or pay for late, once they know its pay to stay it seems easy for me. I watch my cameras around checkout time and would start messaging at 11:10 that housekeeping is on the way they need to get out. I have not had to do that yet though everyone leaves on time or pays to stay until 1:00 since I started messaging that. It is also in my house rules so if they pulle what this guest did I would have recourse to collect. Obviously this guest has no money though.