From what I’ve read you increase your skills faster when they are lower. So you will lever faster using skills you are very unskilled in, thus getting your single stat boost and a new perk quicker. Now for the perk hungry player he (or she) may decide to use only their lowest skills at all times to gain levels and perks faster. The problem is they will remain fairly low skilled overall. Add to that many of the better perks will require a minimum skill level, which they won’t have. Thus a broken character is created, getting clobbered by high level monsters.
Personally I liked having a starting class and boosted skills that helped the way I knew I would play that character. This of course can also create a broken character if developed wrong (Alchemy).
I would point out thought that either the Skyrim or OB character would work fine if you stuck with your class or desired skills and just played the game. The main difference would be the OB (or MW) character would start out better prepared to play the part and could easier fit into any role-playing background you made for yourself.
Thoughts?