Is there a way to make the game actually display what number a skill has increased to when increasing certain skills? The fact that the game doesn't show what level a skill is at makes it rather difficult to keep track, and it's quite annoying to have to constantly enter & exit the character's Journal just to ensure that I'm not over-training something.

There is, the most comfortable method would involve nulling the string game setting that displays that message, and an OBSE OnSkillUp handler that displays more info.

http://www.mediafire.com/?ru5qvtder50yhn3

Requires OBSE. If you have MenuQue installed as well, you should even see the icon of the skill in the notification message.