Ramshackle, as this is the T&T board, I'm guessing that Jet has already settled on what system he is using, and the question is a T&T-specific one.
I've only played two-player so far, so I don't really have any experience to relate regarding good tips for multi-player.
As for good Colonial character figures, I don't think you can go far wrong with Mark Copplestone, either his own ranges, or the Darkest Africa range he sculpted for Foundry. I haven't seen much that is better.