Yeah, you're right. I should probably revise the way I classify such games. Maybe in terms of complexity: Lands of Lore would be the least complex game because of its rather shallow RPG system, while Wizardry (I've only played VII and VIII) seem to be mechanically the most complex. M&M would fall somewhere in the middle because, while not being completely shallow, it is simple enough to focus on exploration rather than combat mechanics.

As someone who picked up classic dungeon crawlers relatively recently, I say that the series is very much playable and enjoyable nowadays from MM3 and onward (MM1 and 2 are both mechanically and graphically dated IMHO).

There's great replay value (though as someone else pointed out, an run of the entire series would take thousands of hours, so I wouldn't care too much about replayability), as you can try the games again with different group compositions (there's also random loot in containers which gives a vague Diablo-ish satisfaction). Plot is mostly linear, so there is no branching plot induced replayability (like in Baldur's Gate series).

Graphics are pretty good IMHO, obviously they are dated but they have this nice retro charm which I like.

Also the story overlaps with HoMM series, which is a nice bonus I guess (though it's very convoluted).

The only downside is that when it comes to MM 3-5, their respective manuals are rather lackluster and you need to find guides online in order to better comprehend their mechanics.

I haven't played Lands of Lore, but the original Dragon Quest is probably simpler than that. Akalabeth might be technically simpler (I am not sure on that), but Dragon Quest is simple in a way that makes it more accessible; simply starting near a town and not having to worry about food makes a big difference.

(I believe one of the reasons Dragon Quest did so well in Japan is that it took a genre that was popular at the time and made it accessible to more people.)

I always recommend LoL as an introductory game to people who haven’t played any games from the blobber genre. There are only three stats (might, magic and rogue) which increase automatically by using weapons/spells, and the playable characters are premade. There is no complex itemization – just use whatever weapon/armor gives you a higher attack/defense number. On top of that, the 2D graphics are gorgeous and have aged quite well. The overall production values are also pretty high, so it’s a nice way to ease someone into the genre.

M&M is similar, but the itemization in 3-5 can be really obtuse unless you have a guide handy. You also don’t have a very clear goal. But, as I said before, exploration is central, so that was probably a deliberate decision on the part of the developer.

I remember wanting to play through the Might & Magic series.

5 years later and I've finally finished.

Congratulations!
The series was my first purchase on GOG. M&M1 made me feel like slamming face first into a wall, didn't go further since, since at first I kept saying maybe I'll try that again, then that maybe I'll give 2 a chance before moving further, and only these days finally decided to give up on the thought for good and just look from 3 onwards, but no idea when or if I'll actually do that. So may just be left with 6 and the early part of 7, played around 2006-2007 or so.

Have to admit, I played the first one on NES. Found it to be superior in numerous ways. Of course that meant I couldn't import my characters but that was well worth the trade-off.

What are character import paths throughout the series? I mean, if you don't play on the NES ;-)

It may be superior in numerous ways, but it also suffers from what I'll call the Locust Plage bug.

Short version: If a Locust Plague gets a turn while in melee range, Game Over.

Long version: The Locust Plague enemy is unfair in the NES version. This enemy, which notably is fast enough to act before your party (at starting stats, at least), will deal 255 damage in the NES version. (In other versions, this enemy is a bit more reasonable; it can do 10 damage maximum per attack.) This is going to KO whoever the plague decides to attack, at which point, due to a bug, the enemies get an extra round of attacks. In this extra round, the Locust plague will, again, KO another of your characters; this cycle will repeat until your entire party is dead. Do you think this is fair? (I am suspecting an integer undeflow bug here.)

You can transfer from 1 to 2.

If 4 and 5 are installed on the same computer, they can be combined into a bigger game called World of Xeen. (Note that the GOG version comes with the games already installed.) You start in MM4, and by using pyramids, you can travel to and from MM5. (Note that spending a bit of time in MM5 might break the balance of MM4, so if you want MM4 to not be too easy combat-wise, I recommend not entering any of the pyramids until you have defeated Lord Xeen.

Edit: I believe that's all of the import paths.

It's been at least 5 years since I played it but I don't remember having that issue. Either was lucky or just kept at it.

I think you can import your party from 1 into 2, then 2 into 3. If you're playing one of the computer versions of course. I LOVE being able to import characters or parties from game to game, so that was the only major issue I had with playing the NES version. I suppose I could have used some sort of Hex editor to 'import' them in a way into 2 but I just roleplayed a new party.

World of Xeen was great... and I can only imagine how awesome it was at the time to combine 4 & 5 into one huge game. First time I experienced something like that was with Sonic 3 + Sonic & Knuckles.

Pretty sure you can't transfer characters from 2 to 3; 3 drastically changed the way the game and engine work, so a transfer wouldn't work that well.

You're right. I think I believed that because the story/manual seemed to suggest you were playing as the same party of adventurers.