I've played 2,3, and 5 (started with 2), and have heard several first-hand accounts from friends I trust about 1 and 4. In my opinion 3 was when the series peaked, and with the two expansions was a damn good game (with some truly excellent user-made maps). HOMM2, while still good, had some unbalanced aspects that 3 fixed up pretty well (speed 6 ranged units, especially titans, were overpowered, and ghosts just completely broke the game; factions were also unbalanced, with knights and barbarians pretty much getting shafted). I passed on HOMM4 based on what I'd heard about it, so I won't comment further on that one. HOMM5 wasn't bad, and incorporated quite a few nice ideas, but for some reason just didn't grab me like HOMM3 did (maybe the pace of it just felt too slow). From what I've heard of the first one it was mostly just a less-refined version of HOMM2 with the highest tier units even more overpowered.