gutter2d: I want to play through the campaigns in the HOMM 1-5 series. I played HOMM 2, 3, and 4 a lot growing up, although never bothered with the campaigns; and am a huge fan of HOMM 2 and 3 (hated 4). Should I just start with HOMM 2 or play through HOMM 1 first?
Having played it again recently, I would say that it's worth it. That said, as EvilLoynis points out, you have to keep in mind that it's the first game of the series and isn't as refined as the later games. There are no hero skills, just artifacts. There are fewer troops per town. There are no troop upgrades.
That said, its visual style has a very appealing charm that will remind you a lot of the World of Xeen from the M&M RPGs. The plot isn't particularly deep, but the campaign is fun.