I still have my Heroes 2 box, and play it if not regularly, then semi-regularly. (I usually go through at least 1 Heroes 2 phase per year, lasting a month or two.)
I only wish there were more maps. Quality maps. All maps I've tried to download online has sucked so bad I've only loaded them up to then discard them. People either don't pay attention to the strategic aspects of a map, or - and this is true for 100% of all the maps I've downloaded - the hobby architects don't pay enough attention to detail in their map building. A map that is strategically interesting is nothing without attention to detail.
I've built many maps (in lack of good new maps), and my latest project is a full fledged XL map, with attention to detail in every single square on the map. It's taken me months to complete. I've only to 'export it' (find it in the maps catalogue on my HD - I have no idea what the title is; while loading it up in the editor works fine, finding the actual file is a hazzle since you can't choose to just 'save as' a new filename). Will post it here then.
Hereos 3 is also OK, IMO - easily the second best in the HoMM genre. Heroes 1 is cool for trivia purposes, since it's basically "like Heroes 2" but with worse (though very comical) fighting and less action items/monsters/general stuff available on the maps. (Obviously, it's Heroes 2 that's "like Hereos 1 only waaay better", but I prefer to see it this way). I enjoyed Heroes 3 shitloads when it came out and played it very much, but nowadays, I much prefer Hereos 2 due to the cozy graphics and general feel of the game. I remember vividly thinking the Heroes 3 graphics to be awesome when that came out, but now, it's mostly embarrassing - but Heroes 2 has stood the test of time since it has very cartoony graphics.
Heroes 4 sucked donkey balls. I only played a few maps before I got tired of it. The whole system integrating the 'heroes' into the battles like that = *beeop* does not compute. I remember liking the graphics a lot at the time, but the gameplay didn't meet up to my expectations.
Heroes 5 was OK in my book, but not much more - then again, I've played this about as much as I played Heroes 4. IMO, the deuce just can't be beat.
I'm thinking about getting Kings Bounty, though - hear it's supposed to be pretty cool. (Obviously, not the original Kings Bounty, that was the founding father of the HoMM series, and is cool for trivia purposes but not much more - but the new ones.)