So, in a scenario where Henry VIII marries Elizabeth off abroad (ignoring the tangled legitimacy questions for now), who would be reasonable guesses/choices to be sent with her as a part of her entourage?
As for who would accompany her? Any female member of a sufficiently prominent and ambitious family would probably see it as a chance and a significant honor.
You've got more trouble than just legitimacy here. She was born in September 1533, which means the earliest (legally) she could be wed was 1545, two years before her father's death. Who wants a protestant girl at this stage of the game? Henry's broken with the church, but daughter Mary is still doggedly Catholic and to keep his church, he's got to send Mary away first.
Yeah, I know, I was looking for specific people though. Would she have men in her entourage?
Maybe one or two, but most likely she'd have mostly female attendants follow her to her new husband's home country.