My experience is that my regulars are happy with $250 for their time (that includes tip). These are the guys I hang out with once or twice a month. I give them a little extra over the holidays or around their birthdays.
I have another ‘regular’ that travels. When he comes to town, about every six months, he stays overnight for $500. I provide dinner and breakfast, gym and laundry facilities etc.
He likes the arrangement because he gets to avoid paying $300 (or more!) for a hotel for that night, gets free meals and can take care of his gym and laundry needs.