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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?
I would say to play it only if your a fan of nostalgia because if you have played H3 or even H2 for long then going back to when the things you liked about them were not there would otherwise leave you with a bad impression.

If you are a person who can keep it firmly in mind that this was a game that was made back in 1995, and really can't compete with today's graphics and does not have even the depth of H2, then sure take it out and enjoy. Otherwise don't as you will just be disappointed for the above mentioned reasons.

I actually have NOT tried 1 although I would like to someday. It's just that I first saw a friend playing H2 WAAAYYYY before I ever got a computer so didn't go back in time to find the first. And since it costs 10 bucks I just can't be bothered with it as it really just should be packaged with H2 not have to be bought separate.
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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.
Thanks! I started playing over the weekend and got midway into scenario 3 before I couldn't play anymore due to my game crashing after every battle in which the enemy hero cast the spell Armageddon during the battle (Note, I don't have the GOG version...I own the HOM Collection Version). But it was a good time until that and it definitely holds up today. I'll buy the GOG version the next time it is on sale so I can continue playing.