Who else has a habit of restarting over and over again?

Not me, why do you do this exactly?

for the most part, the character just doesn't click... something isn't right so I try again to build./roll one that fits/works for me

I do this all the time especially in an RPG like Fallout and The Elder Scrolls I have a deep interest in character design in video games so I could spend 5 hours just making a character and then making a new one over and over again. But I also do it because I can't seem to get a character that fits well with what I want to do even though I don't know exactly what it is that I want to do. Sometimes I'll be playing and pick up a set of armor and be like "I wonder what this looks like on a girl/guy." Then I will start a totally new character just to try on that armor piece. So don't feel bad because your not alone just keep making characters until you find one that clicks. I compare the feeling to running into a locked door in a small room over and over again and then suddenly the door opens up to a huge world. Its a satisfying feeling to finally get a character that you like eventually you will figure it out.

Sincerely,

Prizrak