Ynysley

Is there a painting requirement for the tournament?

Bonus question: Will (reasonable) proxies be allowed for things aren't out in 3E yet?

Generally I'll end up switching at least one of them out during a game, and as you say, the flexibility they provide is well worth the 2ss investment. Need to prevent a key target from escaping? Retibutions Eye. Nekima about to land in the middle of the enemy crew? Fears Given Form. And so on. But even the free 1AP on Dreamer if Nekima goes down early can be pretty good - summon a Daydream/Alp to turn that AP into several, and a single extra waking can mean sneaking in another Chompy activation.

I've recently been paying with something like this and it's gone well:

Grown Up with Big Friends (50ss)
The Dreamer (cache 3)
    +Growing Up 1ss
    +Sleep Cycles 2ss
    +Tantrum 2ss
Nekima 13ss
    +Thousand Faces 1ss
Hooded Rider 10ss
    +Thousand Faces 1ss
Lilitu 7ss
Lelu 6ss
    +Satisfying Punishment 0ss
Mysterious Effigy 4ss

Turn 1 Dreamer will spam Daydreams, I'll drop 3 if I'm able, or settle for 2 and a walk up. Turn 2 he can summon more and/or charge in to bring out Chompy. You're relying on your Nekima/Hooded beater team to clear while Dreamer and Lelu clean up, with Lilitu putting the enemy off position or forcing them to waste cards when you cheat face down.

Most of the time Dreamer is acting as a support, either bringing in Daydreams to harass the enemy and waste their AP, or giving Fast to the twins, or making sure he's in position to heal the rest of the team. Once or twice a game though you'll see an opening to unleash 7AP of chain-activated whooping on some unfortunate soul, and even the threat of that keeps people on their heels as you move around the board.

What is the policy on unpainted models? I'd like to come but my crew isn't fully done yet...

She's amazing with Ironsides. M&SU (and Academic for the mages) makes her work well with everybody else in the crew. I'm usually spending actions on Summons to vaccuum things into engagement with Ironsides and make them Liable (which at that point might as well read "useless"). Hands out slow, insignificant, discards, and generally makes it difficult to accomplish things while she's around. She is a swiss army knife of enemy annoyance.

Rasputina's model pose has always reminded me of someone standing on the prow of a ship. Change out her hat for a bicorne or a peaked cap, and her coat already looks suitably "captain-ish". December Acolytes use an assortment of harpoons to go along with the theme, and Wendigo's pose could have him hanging from the rigging... add a tiny first-mate's cap to the Ice Golem because that's a great visual. 

The first thing I think of for pirates is Perdita and Co.