Hey, your friend was just in my home turf! I've seen their work before locally. I guess they must come down here often.

I would suggest doing the glass first, then paint, and then coat it with epoxy. The issue with painting first and then glassing would be that the epoxy would not be bonding to the wood. It would be bonding to the paint. The bond to the wood would be the paint. Acrylics don't have as good of a bond as epoxy, so that would be a weak link.

I just did some test with automotive pinstripes to see if the epoxy would leach under the pinstripes and bond to the wood and it didn't. Although with the pinstripes being very thin I still got a very strong bond, if I cut the glass with a razor along the pinstripe I could peel the stripe up. I think the same would go with acrylic paint- it could start to peel away over time and the whole glass job would come with it.

A lot of people I know have used watercolors and watercolor pens on surfboards and glassed over it with no problem. The watercolors absorb into the material so the epoxy still gets a good bond with the material itself. I don't think watercolors would work as well on wood (unless a very light wood.)