According to TMZ, some of the privileges that Bruce used to enjoy will not be available to Caitlyn, simply because she's a female, which is pretty upsetting on a lot of levels.
The site reports that the main dining room and bar are male only and are actually attached to the men's locker room, where women are obviously not even allowed. There is a women's restaurant, but it's apparently not as nice.
As if losing privileges won't be upsetting enough, this would make it tough for Caitlyn to hang out with the male friends that Bruce made at the club over the last 15 years.
The good news is that Sherwood is open to Caitlyn filing an appeal and they're currently closed for renovations until December, so they do have some time to work things out.