I like the novel way you're implementing it. It's charming and has quite a bit of potential... Personally, I love these waitress type (mini) games!
For the Bar version, I'd like to see the possibility of her accepting drinks from the customers for more scene possibilities (general harassment, bathroom scenes [not watersports or anything like that, I mean], or accepting a customers help to escort her drunken self back to her room after her shift / or mid shift)