I've found that the biggest hurdle for people enjoying Oblivion or Morrowind is whether the player is able to develop a comfort level with the game. If they get to where they
feel like they know what they want to do, where they can go, know the surroundings, how to develop their character, how to handle the many story lines, how to fight, and even happy enough with how the game runs on their hardware, then they frequently get sucked in to the massive freedom, huge scope, and diverse possibility of the game. In other games, rigidly linear story lines will define progression in the game and pull the players interest through while such comfort levels develop. This also simplifies a game so much that it is much easier to become comfortable. Oblivion and Morrowind do not really have this type of situation to help people get started.
In lieu of Oblivion and Morrowind not simplifying getting started, I would recommend to a player having trouble getting into the game to just focus on whatever the next step is in the main story line and try to accomplish it. It ends up being more like starting a typical game and helps people get going. At some point, a player will generally want to either start branching out or start over with a new character. A good second step from following the main story line is starting quests for a guild. It's what I ended up having to do in Morrowind when I played it the first time. I loved what I saw of the game, but I felt lost. I didn't know what was out there, where was best to go, or even how I was supposed to try to fight other than obviously swinging a sword. So, I just jumped on the main storyline and rushed into it. Eventually, that got a little tough for lack of character development, so I started the Thieve's Guild and had lots of fun with that. By then, I started getting comfortable and creative on my own, and having tons of fun.
As far as Oblivion or Morrowind being better than the other, I've found that people who have played both frequently have their opinion formed largely out of that comfort level they may or may not have developed with each game. A lot of long time Morrowind players have trouble developing that new connection with Oblivion when they can pull back to Morrowind and get much the same type of gaming experience. Also, I have known several people who played Oblivion without even knowing that Morrowind existed. After loving Oblivion so much, they found out about Morrowind and bought it too, only to have trouble being able to even get into the game without wanting to just play Oblivion some more instead. Being as objective as I possibly can be, I think the two games are pretty much equal for their time. Going from there, taking the "when they were made" element out of it, I would say Oblivion is better thanks the more advanced technology and maybe more detailed content. Of which one I have enjoyed more personally, it would be Morrowind because I've had much more time that I played it. Someday, if I can get enough time to play games, I will likely switch that over to Oblivion...a newer, higher powered PC wouldn't hurt at all, either.
