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What is the best game in the series to start with. I have 3 from gog as well as 5 and 6 from steam. I am on the third mission in long live the queen and having major difficulty with homm3. I think the problem is I didn't build my heroes well.
3 seems to be the fan favorite, so if you don't have the earlier ones, I'd stick with it. I first tried 2, but I've dropped back to 1 to play them in order, and while it's fairly basic (and its spellcasting is rather flawed), I think playing it does help you get an idea of what the most central ideas of the series are. As I understand it, the first three games pretty much built upon the same core mechanics while the later installments started experimenting more with the formula (which you may like or not according to individual taste.)
Heroes Chronicles is the easiest of the HoMM games and may be a good start.
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PetrusOctavianus: Heroes Chronicles is the easiest of the HoMM games and may be a good start.
The only/major downside to Chronicles is that it's Campaign ONLY. BTW Chronicles is basically Heroes 3, they just created some great story lines for Tarnum.

Heroes 2 or 3 are best to start with imho. Heroes 1 may even be good but I would not recommend playing them in any order but that which they came out. The reason is that if you start say with H3 and like a feature they added in it it's going to be kind of annoying to go back to a time when they didn't have it.

Also 1,2,3 & 5 have much more in common with each other and are a logical buildup. The only problem I really have with H5 is the 3D but hey others like it.

Heroes 4 can be played in before or after you play any of the others because they totally revamped the game. In some ways this was cool but in others in suffered. It doesn't really feel like part of the series except for having the same towns/Heroes and continuing story line. Most of the problems people had with H4 would not really have been issues if they hadn't played H2&3 first, or if they had made it it's own game.
If you play HOMM for the campaigns, I recommend HOMM2 as I feel the campaigns there were better (and harder) than any of the other HOMM games.

There is still a case for starting with HOMM1 though but you said you already have HOMM3 from GOG so this is probably a moot point.. You could see where the series started but if you play HOMM2 or 3 first, it will be hard to go back as HOMM1 hasn't aged well at all. I have the CD version of HOMM1, finished the campaign with all 4 factions but I doubt I'll ever do it again and I'll probably only get it from GOG if it was included in a bundle.

IIRC, the only difficulty I had in any of the HOMM3 campaigns was the evil campaign in the original HOMM3 but that's because I was sticking to one factions units and not combining the strongest units from the dungeon and inferno factions. HOMM2 campaigns were definitely harder. Really wanna play HOMM2 again.

As EvilLoynis mentioned, the revamped HOMM4 completely so you don't need to consider this one when comparing features in the other HOMM games. Some people liked it, some didn't, I am one of the former as I think I've spent more time playing HOMMIV than any other game in the series.
Post edited December 23, 2013 by IwubCheeze
If you wanna learn to play the basics of the series, either the second game or Heroes Chronicles.

The second game's colorful nature and its heraldic, "color coded for your convenience" looks makes it easier to learn the basics of the series. It also has most of the elements that would become staples in the third game, but in smaller quantity... meaning it's less stuff you need to learn and memorize. It's also one very beautiful game in term of graphics and soundtrack, and the main campaign gives you a certain degree of freedom over what mission you want to play next, which is sadly missing from the third game, meaning not only is it a good game to learn the basics of the series, but it's also a fantastic game that typically trump the other games in the series in all aspects except for the cheer quantity of monsters, factions, spells, skills, etc.

That being said, I won't deny that when I switched from Heroes of Might and Magic II to III, I had to put the training wheels back on as while I knew the basics, I still had to learn a new set of monsters, spells, heroes, artifacts, factions, skills (and if there is one aspect where Heroes of Might and Magic III shines in it's definitely in the sheer quantity of everything it has)... plus master a couple new elements added into the game, notably the new Wait function in combat, the terrains and their effects on the battlefield, the specializations of each heroes... I suppose it can be done during Heroes Of Might and Magic III's Restoration Of Erathia campaign, but I found it easier to get used to all the new things by playing through a couple of Heroes Chronicles games, which only introduce a couple factions and elements at a time.

But yeah, Heroes of Might and Magic is a strange beast in that the third game is the meat of the series when it comes to depth of gameplay and the sheer quantity of game elements, scenarios and campaigns it has, if you had to play one game and only one game in the series, that would be it, but at the same time, since it has so many elements, it can be overwhelming for a new player who has to learn the basics in addition to everything else.

I haven't played the fifth nor the sixth games so I can't really comment on those. As for starting with the first game, the first game is simply too bare in my opinion and lacks many of the elements that were introduced in the second and third games that would become staples in the series: the spell points work differently, castles have no moat nor gates, making breaking or defending a siege more complicated for a novice, the factions are very unbalanced, the secondary skills are missing entirely, and the graphics are not as charming as in the second game. It also has a token plot meaning it is not necessary to play the first game to enjoy the second or the third games.

But my family and friends learned the ropes of the series with the second game so I might be biased.
Post edited December 23, 2013 by blueskirt42
Go for heroes3, heroes2 might feel outdated, heroes3 is a perfect game just like chess or checkers. After that you will dislike other heroe series i almost guarantee you :D

Heroes 5 is pretty cool but the "fog of war" is a big let down. I think this game should not game fog of war.
Id say Heroes 2 or 3.. both great.
i would say you should start with heroes 2 , i personally liked it more than 3
I think you should choose between HoMM 2 & 3. Just start each one and choose whose overall visual style you like more. They are very similar in terms of gameplay basics.

Personally I prefer HoMM 2 mostly because of warm memories of youth :) The third installment appeared when many other decent games came up so I never had enough time to play HoMM 3 all through.
Post edited March 13, 2014 by Rodor
I love Heroes 2 and 3, but I think 3 wins for me.

I would definitely try 2 if you haven't.