1. Can't go wrong with the Heritage, get it you'll be stoked. The kind of riding you do, the infamous NS bombproofness will last you the rest of your life.
2. If its between Flow and GNU for bindings, Flow hands down. The GNU and K2 rear entry bindings are behind Flow big time in the game, while Flow holds its own with traditional bindings. I've tried all the gimmicks the last few years and I find that I am back to preferring traditional laces on my boots and traditional 2 strap bindings. I would prefer the Cartels you mentioned myself.
3. Vans don't get alot of love as a boot but I have always loved them as a company and shoe. They fit good?