As a lot of fellow players have said in here, I think specialists are far better and more interesting than generalist characters (jack of all trades). Imo, they are easier to role play, create a back story, and give you reason to try different characters later on, specialising in something else.
2 exemples here... First, you are a Khajiit, thief/assassin, who cannot get in walled cities unless it's night time and you sneak in (putting points into sneaking, one handed for daggers, archery, alchemy for poisons, maybe a support skill like speech or pickpocket).
Another one, you are an Altmer mage, who actually hates the Thalmor. You will hunt every single one of them because they made you flee from Summerset Isles, but you also hate Nords, as they hate elves back. You will rise in the College of Winterhold, putting points into whatever magic schools you like (for me, Destruction and Conjuration are always a must).
So, with this you can have completely different characters, which makes the game fresh. After you have completed which ever was the goal for that character (like becoming Archmage and getting all Deadric artefacts, let's say, you can jump to another one). That's how i like playing.