I'm actually thinking about doing a three game playthrough with one character starting in Morrowind, and transitioning into Oblivion then Skyrim. This would be the same character, same race, class, story, etc. But that is irrelevant to this topic... I'd also have to buy Oblivion again and I don't really want to spent $20.
Character Creation:
Creating your character in Morrowind is the ultimate display of beauty on the inside. Your character';s appearance is about as shallow as modern day pop culture. Most of the time you're a cookie cutter character that is more or less a reflection of the NPCs you interact with. There are some cool features like the Female Bosmer having butterflies in her hair (I'd pay like $2 for that as DLC despite never playing female characters), but most of the time it doesn't matter as you';ll be covered up by armor. The real beauty if what your character is made up of. There is a certain addictive quality to creating your character. However after that first run through it became like the equivalent of taking a test, I've started studying for when I create a character. I run my guild through external sites in order to get an idea of what I want. It becomes like trial and error, the sad thing is you can go through around half of the game before you realize that this isn't the build for me. To cope I've learned to not become attached to me characters as I know I'll just start a new one half way through. The nice thing is I've progressed further and further with each new character, getting around half way done with the main quest and mages guild before making a new character.
I understand the weird high I get when I see stats flashing on a screen, which is why I become so addicted to games like WoW, or torchlight where loot becomes a huge part of the game. Mixing and matching different armor combinations to get different stats, and bonuses becomes almost addicting, however it can also lead to a ton of trial and error. With WoW you had the ability to reset your skill trees, which is almost necessary given the balance tweaks they do. In Morrowind the only way to reset yourself is to start afresh. When researching build ideas, testing builds, and creating builds exceeds the time that I actually play the game I know I have a problem.
With Skyrim I could make the character look like godzilla, or a troll for all they care. The attachment to your character becomes a more physical bond as you learn to love your Gandalf look a like, or one your eyed warrior. Your quality feels unique aesthetically, you feel like you're a your own person, rather than a cut out of some npc. However from the get go your character is different in looks, rather than talents. You're not longer unique based upon your race, or your class. Yo're in a way just one class, and one race. You may have some innate difference in starting spells, or what skills you have leveled, but it never affects your character. Although my Orc may have a little bit more heavy armor "skill" he is at the same level as a Khajit who may have slightly less. Skills don' really have that much of an affect on your character, your perks handle most of the bonuses but the skills points are the criteria you must meet to actually grab a perk.
This style allows for more flexibility over time as you're never restricted to what you determined at the beginning of the game. You could go through the first 5 levels without getting any perks because all the races play almost exactly the same. Your characters destiny is never set in stone, they're never restricted to one skill or the other. In Morrowind you could be screwed easily in the beginning because the AI isn't rubber banded to you, via level. You could effectively gimp your character for the rest of the game without knowing it.
Characters:
Before you start fighting all your epic dragons, rats, and other dangerous creatures you're most likely going to meet a nice man who determines your future. You may even meet his friends who may or may not like you.
Morrowind tends to focus on more realistic characters. I've yet to meet a character who is basically a cartoon crazy man. The different races feel like they all have different personalities, which I enjoy. However non really stand out to me. The same was true for Oblivion I can't really remember any of the characters.
Skyrim is... interesting. Since it';s fresh in my mind I can remember quite a few of the characters. The room for voice acting allows for a lot more personality to come through, however at times it become a mess. Characters personalities range from Astrid who has this very subtle, dangerous tone to her voice. Accenting words that really enhance her dangerous persona. All the way to guys like Cicero who are just stupidly over the top. There are a host of good, subtle, strong characters and a range of just stupidly annoying characters.
TES has never made me fall in love with the characters... unless you count the world as a character. I don't spend extended periods of time with them like I would in a Final Fantasy, Dragon Age/Mass Effect game, or Shadow of the Colossus, which means I don't ever develop any bond with them.
Combat:
To say that Morrowinds combat is slow is an understatement. To say that Morrowinds combat is terrible is an overstatement. The combat doesn't feel as fluid, or immersive as Skyrims, but that can be attributed to the ways games have evolved, and the progressions Bethesda has made as a studio. Coming from a long time Final Fantasy player the combat is very similar to Final Fantasy. However the problem becomes the hit boxes being somewhat terrible. Within a Final Fantasy game the combat was turn based. I said attack, he/she attacked. Depending on the Dodge rate of the other character, I'd hit or miss. It also depended on whether I was blinded via, a spell, and do on. If the character dodged my attack the character would step back, or give a sign that it dodged.
In Morrowind there is no such thing, there is no animation for a dodged attack. You end up slicing at air wondering whether your aim is off, or if your agility/weapon skill is too low. This is most noticeable when shooting a bow, or hitting smaller creates... OR when you're trying to attack one specific enemy when there are two or more, or when you';re trying to talk to an NPC in a crowd. Also you get caught on every single piece of geometry in the world.
The addition of a dodge animation would make the combat more fluid, responsive, and immserive. It's inexcusable for a game to lack a feature in which the hit/miss mechanic is based upon percentages. Even in Final Fantasy the doge animation was merely the character teleporting backwards, and then forwards. It had no where near the fluidity of animation today, but it was a sign that they had dodged.
The combat in Skyrim is much more immersive, and much more rewarding. It's something you tend to look forward to, rather then dread depending on how you built your character. The lack of outside influence (such as dodge, or hit/miss) means it's based upon your skill rather than your stats. The one area that the combat is lacking is in depth, the game becomes more a hack and slash rather than a strategic encounter. I'd much rather see more development put into creating a more engaging experience, or see it become turn based because as it is now it is stuck somewhere between Dragon Age, and Dynasty Warriors.
For all my negativity towards the Morrowind combat I'll say that it isn't that bad. It can be especially fun, and rewarding later on when you've honed your character into a killing machine, but that's dependent on whether or not you can even get to that point.
Story:
Can I just say that I';m not a fan of either story? I love the way that Bethesda works its players into the lore in the move ambiguous way possible. But for me the story has always been me, and what I've done in the world. The main quest is just a footnote in the overall story that is my character. I saved the world!... But I also become the master of the Thieves guild, and the champion of the Arena. That's the story to me, and in that way the stories in Bethesda's games are some of the best around. But for the overall main stories I'd say they're never all that interesting. A lot of the Deadric quests are awesome, but the main quests, and even some guild quests, are sub par.
Real World issues:
One of things I enjoy about the TES games (and many fantasy games) is that they can handle issues that other games rarely touch. These things would be Racism, sixism, Slavery, Religion, and so on.
In Morrowind you're hit in the face with the issues of Slavery, and Racism right away. Fresh off the ship you're seen as an outsider, or outlander, you're not liked because you're different. That coupled with the fact that the world you're forced into has a large slave trade and the atmosphere of the grim becomes more real, dark, and intriguing. I enjoy this, not because I'm some sadistic a-hole, but because I find that to be an intriguing plot device, or tool for immersion. Religion is another interesting factor in TES and I feel Morrowind handled religion the best. You truly feel the sense of religion in Morrowind, it's never really forced (you don't hear people praising Talos every second), but you feel the weight of religion, and the way it influences the different mechanics between temples, and cults. It's also nice that you can join temples and feel like you're apart of the religious atmosphere of the game.
In Skyrim you get a similar scene, although slavery has made its way out. Racism is taken to another level in which it doesn't make as much of an impact on how NPCs view you (they still have an opinion of you, although it doesn't hold the same repercussions that it did in Morrowind), but it's taken to another level in which segregation occurs in some cities. sixism is present to a degree in the game as well, however it's as in your face as the racism. As far as religion it has taken a backseat to a degree. Your ability to involve yourself in religion has been greatly reduced. However the ban on talos makes for a very interesting, somewhat strained relationship between the Thalmor and the citizens of Skyrim.
Overall I feel like both handle somewhat different issues, and take them to different levels. I'd love to see more done with these issues, as the issue of religion is very interesting, especially in a world with so many different gods, or deities. As it is now the different issues have very little depth, and player interactivity, especially with player involvement.
Conclusion:
I feel like both games provide different experiences. In a lot of ways there are some things about Morrowind that bug me, much like there are things in Skyrim that bug me. However for me there isn't anything in Skyrim that can potentially ruin character creation, and inevitably the whole game. Morrowind feels like a 100 hour game that should be a 40-50 hour game. When re-rolling a character becomes a chore rather than a fun way to start fresh then I know I have a problem. That to me is what really holds Morrowind back. I understand that some people like the trial and error mechanics but it just makes the game bloated. In Skyrim I end up making a new character because I want to play the game differently, not because my character has become inept.
For some the redeeming quality of Morrowind is its story, and depth. The story is lost on me because as I've said the story for me is my character, and I'm really not attached to any of my characters because I know I'll just up re-rolling. The game can be truly deep, and at other times it's basically re-arrange numbers to fit what you want.
I like both games and am enjoying Morrowind. However I enjoy where the TES series has from and also where it's going. For me Morrowind is the game I sink maybe an hour or two into before getting bored, frustrated, or burnt out. Skyrim is a game where I can spend hours just messing around and being immersed in the world. Morrowind is dated, no matter how you look at it. A lot of the hooks that developers use today are beautiful and work maybe too well. For me Morrowind doesn't allow me to RP, or become immersed in the world.
Maybe I'll finally make a character I truly enjoy and can feel like I want to invest my time into. But for now I'm fine with just repeating the same process until I find that character.