that journal was intended somehow as a day by day diary, not a quest log (like it becomes a little with the Tribunal expansion), so, when I was reading it, after months without playing, I was mentally living again the routes and the events in the order that them happened, not just a:
"Quest done, don't mind"
"Quest todo, let's see where to go even without remembering the background"
"Quest done, don't mind"
(like in the following Bethesda titles)
It was exactly "this mess" that made that game great for me, the quests were requiring much more attention to details to be completed, by conversations, books and/or clueless exploration, and happended many times to me to take out that journal and start reading it again, to find out that litte bit of info that I needed to finish a long forgotten quest, that a passerby just pointed out.
Also many entries were not clear quests, but clues about "something" you still don't know that just happened... and so, as in real life, you can't catalogue them, but write them down for a "maybe" future reference...
Many games have the "New quest added" thing that I really don't like...
you find a ball, take the ball
[New quest added] - THE LOST BALL - Go to the children at <this address> to give it back]... WTF !
In Morrowind, you find a ball, and if it's something quest related, you'll have a new entry in the diary "Today I found a strange ball, it was made like this and that, I wonder who left it..." and then you are alone, the rest will be discovered if you will find the right people or if you have new dialog options...
Many times happened to me to find out that I was doing a quest without even knowing it, but getting the reward with surprise !!
That was why I, in an unexpected way, started appreciating so much that so confusing game... because I was always lost !!