If you are comfortable bunking with someone and the accommodations themselves then I would go for the two nights. Not sure how far away you are traveling in but unless you are coming from PS itself the travel itself seems to make one night very tiring. I always think of it as a mini-vacation so that a couple of nights make it worth it.
He did a number of videos that were always really hot. If I remember correctly he always got great reviews when Rentboy was around, etc. I think he presented as pretty much a bottom and if you see his ass you see why. His pics seem to be updated from his prior listings and he has (like the rest of us) gained a few years. He would certainly be someone I would feel comfortable hiring.
In most of his scenes he does terrific fucking. I have never seen him bottom. But he does a significant number of breeding scenes if that is an interest.
I can see that the title of the thread is that the escort is in Chicago. However, when you go to his profile on RM it says that he is a performer in NYC. Also the traveling notes are for NYC and Ft. Lauderdale. I was wondering the basis of discussing him being in Chicago?
Oh, thanks for the explanation. I thought perhaps you were giving your typing fingers a rest. I had a time out once. I used it to improve my dildo technique to be used in coordination with your postings when I was freed. In any event, welcome back!