Studio to stage: What do I need to think about?

I have a macbook linked up to a profire 2626, vocals go through an Alesis compressor gate before plugging into the profire, and in the studio I have the following plugged directly into the 2626:

KORG Triton Extreme synth,
KORG Electric Piano,
KORG Kaoss pad

I also have a M-Audio trigger finger for setting off a few loops and things... and at the moment I have Ableton Live software- although am thinking about getting Logic or Pro Tools... and I have Mackie SRM350 loudspeakers.

If I was to take this rig live, what else do I need to think about? I'm thinking DI boxes, but really not sure why, and possibly other stuff that could help limit feedback from the vocals. Also, is Live really the best tool live? (That sounds stupid I know!) Can Pro Tools or Logic be configured with a mixer and the MIDI capability to control effects and things? And would this whole idea be written off by Latency?

Hoping for much insight....

Oh and also....

I have an analogue Compact 10 mixer actually- would that come in handy? (I'd rather not use it cos I struggle to get the best results out of it....)