One More Job - Character Creation

I don't have a preference for city.

I submitted a character sheet. Basically, for this character, I tried to use all the traits that I thought weren't as widely usable as the others (Supernatural, Follower, Introverted, and Pessimist) to see if it would still work.

Silent and tough, Bruce is a hardened veteran driver. Though notably pessimistic, he's managed to pull off incredible stunts in a variety of vehicles and sticky situations throughout the years. Unknown to anyone else, he used to be a normal person, a long time ago. His wife was held hostage by [insert big crime people], and he was forced to drive for them. It was supposed to be a one and done job, but his newfound talent for driving ended up working against him, as [insert big crime people] sought to exploit his skills by keeping his wife hostage. The government agents have promised him that they'll extract his wife safely if he lends them his skills. It's been a long time, and Bruce is tired of waiting for a promise that'll never be fulfilled.

I had a couple of clarifying questions. Can multiple habits stack advantage on the same roll?

Also, a thing that I noticed is that d4s have a slightly better chance of success than bigger dice at the same distance from the center. This probably isn't that big of a thing, since the rules for resizing dice and the points you get in char gen should push the target number further from the center as the dice get bigger in most cases, and since the chance of success isn't that much bigger with a d4. Just something that I didn't expect