I'm in a similar boat as Daox, have a Prius, had a G1 Insight, never driven a G2 Insight. The Insight was fun, but I didn't drive enough to call it anything other than a toy (so I got rid of it for toys that don't require insurance
http://ecomodder.com/forum/showthrea...ike-28487.html). It sounds like you do drive enough, but then there's the issue of fitting your equipment.
If you can get a G1 Insight for $2k and you're not afraid to give it some love, I'd say go for it. If you decide the G2 would work better for you, I would highly suggest looking at a Prius as well. In my area it looks like the biggest difference between a G2 Insight and Prius of the same price is that the Insight will be a few years newer, but they'll have similar miles.