Hmm. I think I'd go with:

Jon $4
Melisandre $4 (if you die, she'll resurrect you, you just need to be a decent enough person not to burn people to death for her)
Tyrion $2
Daario $4
Tormund $1

Jon $4 because of his people skills.

Bran $5 because of the information gathering.

Tyrion $2 because in that field Tywin is best but cost too much and the others are not worth it.

Arya $3 because of her masks and skills so she can do the dirty work unseen and unknown.

Tormund $1 because he is a good fighter and also the leader of an entire group of people.

Stannis
Jaqen
Tywin
Bronn
Mountain

1) $15 - Drogon

B) rape faces

Leader: Jon $4 Pretty simple- he's the only one in this group I'd even bother to follow.

Magic: Bran $5 Have to spare no expense here. He literally knows everything. With him you don't even need a strategist.

Jaqen was tempting because he's ****ing awesome but even he says his skills require time. "Death is certain, the time is not".

Strategist $2. Tyron Who gives a shit who's strategizing with all the information we'll have thanks to Bran? A chimp could lead a successful campaign with the 3 Eyed Raven on our side.

Fighter: Bronn $1 As Clay said, great ****ing value here. He's great in 1-on-1s, large scale battles, has gone beyond the Wall, has experience laying sieges, and isn't afraid to fight dirty.

Brienne would be another steal with the Valyrian steel sword, but I think her honor would get her killed against a guy like Bronn.

Muscle: Khal Drogo $3 Have to go with the guy who's never lost a fight. He's probably the best fighter we've seen on the show outside of Arthur Dayne. I'd have to get him some light armor though.

$2 Stannis Baratheon
$3 Jaqen H'gar
$5 Tywin Lannister
$4 Daario
$1 Tormund

Stannis
Jaqen
Robb
Oberyn
Hound

Wish I had $16 so I could do Drogo instead.

Jon Snow - $4
Bran - $5
Robb Stark - $3
Bronn - $1
Hound - $2

Although you could make a case for the following.

Dany - $5
Bran - $5
Robb -$3
Bronn -$1
Tormund - $1

You get the dragons, the three eyed raven, a decent strategist and two good fighters.

Well if the Dragons are included with Danny, then she has to be in everyones.

This, but swap Robb for tyrion and use the $1 savings for Tormund.

Tormund is cheaper.

John (4), Bran (5), Lady Olenna (1), Bronn (1), The Mountain (4)

Hot Pie could be an elite strategist with Bran present.

Robb Stark was a shit commander.

No he wasn't. Robb's downfall was that he was reeruned when it came to love.

Dude took down Jaime at his prime.