Do the careers that say "any race" apply to halflings? I know they apply to ogres because they could be chosen by a human or dwarf, but it doesn't necessarily meet the rogue/menial requirement of a halfling.

Depends on the GM I guess, but I'd probably say yes if the player has a good reason for picking that career.

I'd assume so. I mean halfling IS a race so it's no different than if the class said "human, dwarf, high elf, wood elf, ogre, halfling"