I've used the create character trick to increase my gold so $$$ are not a problem. I do have the following questions though.

1) Is there any disadvantage to creating party members that are immediately eligible for training to elite roles? I'm starting with a Barbarian, Sumurai, 2 Warlocks, a Monk and a Paladin.

2) Is there any reason to start with a Rogue since a Barbarian can learn thieving skills?

3) This is probably dumb but how do you actually become a Barbarian, Warlock, etc. after you go into training? Do you need to complete a special quest? If so, where do you get the quest?

Thanks in advance for any help!

Each guild will tell you how to complete the proper quest...i'll leave that for you to explore on a per guild basis..

As to going to elite classes right away..I would not do it..
You'll loose out on free hitpoints..and ability points..if you do it right..

You can't become a ninja, samuari, or bard until you hit town 2..I can assure you on this...since the required quest..require you to have the ability to enter certain areas around town 2..

I find it strange..that you know what skills a barbarian gets..without knowing how to complete the quest?
Also..just because barbarian gets cross-over skills..you are going to miss out on rogue specific..and rogue only skills..if you do this..
(Rat's get gold digger..you can't pass up on this combination with a rogue..You won't get any good loot from treasure chests...)
Rogue Rat = essential (In my honest opinion...period)

don't take the quick and easy path..you'll just end up screwing yourself over..

What are the rogue specifc skills? So far I found 0 so I restarted with a Rat Barbaian that I turned into an ninja and assassin further down the road