Undercity and Orgimmar will be the hardest, Silvermoon will be easiest

Are they cool with that?

Hell no but if you're a rogue, its very do-able. Its an actual achievement though

I have a hard enough time sneaking into Org to do the fishing achievement.

Not sure what's going on on your server, but we usually would do For the Alliance and Pilgrims Peril at the same time.

luckily the tables are outside the cities not as hard as goin in unless its the Night elf city lol

Dazz are you a rogue/what level? at 80 you can sneak around anything, I was even in the room with the 3 bosses in Silvermoon and they didn't

see me. The only things you have to watch are the stealthed 80 elite guards in Undercity, and the roof catchers in Orgimmar

but yeah like Dreama said, since its outside it'll be a cakewalk, all you have to do is sit