Barmaid stuff is pretty quick, it's just there to make some quick money to avoid debt or something. The maid stuff is significantly more involved, with little random events with various choices and outcomes, and you can do or be involved in sexy stuff. If you let your debt go out of control you can get sold into servitude, as well. There's no stripper job but you can unlock the ability to dance for people to seduce them when nude. There's also various exhibitionism and flashing options as you go.
You can fuck most major characters aside from Roland (the tavern owner) and a couple more minor recurring characters. Burke is the guy you get the vendor license from, and you don't see him again after that part of the story, but it is possible to seduce him or to trick him into drinking a heat or love potion and then seduce him.