I have never played a HOMM game but I would love to. I am a fan of lore so I would like to start earlier in the series but, I also want a game that is easy to learn. I have had trouble with games from the 90s before because I am kinda a dunce and it's hard for me to learn complex mechanics. I will say I was a big fan of Age of Wonders Shadow magic, which this series seems to remind me of based off screenshots. (Even though I never beat shadow magic campaign because I'm a baddie) But anywho, with all this in mind, what would be my best entry into the franchise?

The first one that works,would be a good start:)

HoMM2 and HoMM3 are both great places to start (and also the two best games in the series).

I worked my way up. They're all good. All of them are different, but with some same core mechanics. If you play 3 first, then you might not want to play any of them.

So if you want to play them all, I'd say work your way up.

If you are tight on time and/or money, pick up 3 and ignore the rest.

2 was my favorite, but only b/c 3 is maybe a bit too big of a game for me.

Good luck!

I would suggest 2. I think 1 hasn't aged very well. I also think 2 is amazeballs.

I have a lot of nostalgia for the first one, but I doubt it holds up very well. The second one should be a good place to start, and the third is where the series formula reached perfection.

You'll probably hear a lot of bad things about IV, but I love it, though it's deifnately not the place to start. It changed a lot, but I think it was the right choice- after III there was nothing to improve upon in the formula such as it was The only thing to do was to reinvent the game, and despite some flaws I think it worked great. IV and it's expansions also have the best campaigns in my opinion.

V was a huge letdown for me, basically a return to the old formula, but uglier and inferior in every way. It's not a terrible game, but it's perfectly pointless.

3 is the most refined one. I heard Heroes Chronicles are easier (same system as 3), so it may be easier to get into.
4 added some new elements, but was a bit less refined in some aspects. The sound track was absolutely amazing.
5 is kind of a return to the gameplay formula of 3 with 3D graphic.

I personally like the refined gameplay of 3 but also love the overall experience of 4. I don't think you can go wrong with any one of them.

HOMM 2 was my favorite too, but as htown said its graphics haven't aged well. I liked it a little more than 3 because in 3 once you found the overpowered artifact, it was all over but the shouting. The enemies had no chance. In 2, the artifact made the hero who equipped it powerful, but you still had to take the fight to the enemy and vanquish them. I mean in 3 the artifact made its owner op, but in 2 the artifact was just an advantage, albeit a big advantage.

Start with Heroes Chronicles. They were designed for new players, and will be boring once you have mastered HoMM 1-3.

Do you know if Chronicles have any widescreen patch like 3 does?

I don't think the Chronicles have much, if any, mod support.
I will be happy to be corrected, though.

I suppose it depends upon how much time you want to spend on the series. If you think you'll only really play one of the old ones, then I'd pick HoMM3, widely regarded as the best in the series. And don't worry about it being too difficult / complex. If you go through the levels chronologically, in the order they were released (ie not lore wise), then the game will gently ease you into the playstyle. The first couple of levels of the base game's original campaign are really easy. Of course, the difficulty ramps up towards the end, and especially with the expansions. I still remember spending a solid weekend trying to beat that blasted 'retrieving the cowl' level :\

Just a word of warning if you do start with HoMM3: From the main menu, the top most campaign is not the original, ie first campaign!
https://i.ytimg.com/vi/0dQ3GcbkTwk/hqdefault.jpg
Restoration of Erathia is. I assumed the top one, shadow of death, was the first one and started with it. I couldn't understand why the first levels of the game were already so crazy difficult :P

The usual suggestions are 2 and 3, I have played them both and enjoyed them. But nobody has unlimited free time so here's what I would do if I started over. I would not play homm2. I would play each of the homm3 complete campaigns once and fast, . And then the real meat of the game begins. There used to be a fantastc community (I don't know if it's still active) that has produced extraordinary campaigns, scenarios, and even mods that add type of towns (cove with pirates and sea serpents anyone?) etc. Your job is to find the ones that you like and add many many hours of fun and challenge to the game.

Start and end with 3.Best by far,great mods too.Has almost everything you would want from M&M universe

2 if you like that old-school hand-drawn feel in a game (I grew up playing 2 and have fond memories of it). 3 if you'd rather have more complex gameplay and a wider variety of races, units and heroes to choose from.

I have to agree however that 3 is probably the pinnacle of the series, so even if you decide to start with 2, don't stop there ;).