Bitch rant: the negotiating and hiring of escorts in the good old days (1970's/1980's) was much less complicated and a lot less expensive (much like everything else, I suppose).
I believe that also identifies him as a bum.
bum
noun (2)
Definition of bum
1a : one who sponges off others and avoids work
b : one who performs a function poorly
Deadline.com has the date as Sunday, January 19, 2020 (10:30-11.07PM), but I don't know if that date is firm.
https://deadline.com/2019/12/curb-your-enthusiasm-season-10-premiere-date-hbo-trailer-1202806663/
Not that it really matters, but my eye was taken by the commitment ring on his third finger left hand in image #6. It doesn't appear in any of the other images.