You don't have to do Skirmishes although you might want to, you can do battlegrounds etc if you really want to do Skirmishes we're gonna have to deal with it sadly.:p
I boosted a 90 paladin I now discover that I don't like playing paladins! So now I have a level 90 paladin sitting there with 502 ilvl and not being touched!
When I am twinking I prefer to be in a guild were there are other twinks that are twinking at the same bracket as me. From what I know off there is no guilds which are seriously preparing for 29 twinks and recruiting 29 twinks. On EU.