I know nothing about Gloomhaven, but I saw the box art and was intrigued. The description sounds really cool. Anyone play this that can add anything?
My opinion for 20$ pick up Tabletop Simulator and play the game. There were a few games going on this weekend in the multi-player servers. You can also always set up a solo play through to check out the mechanics and rules a la Rahdo or others who do the videos.
Jump in the water is fine, that is how I was able to give Gloomhaven a run with the KS 2nd printing campaign.