Yes, you can over time get fancy new gear, collect resources, gain experience and favours or just loot things off corpses. but if your question is, 'by the time this is done will I be a meganob', probably not. 

The problem with something like a kommando is it works best if everyone else was making a kommando as well. I don't like splitting the party and having to keep track of people as they run off in a dozen different directions. I'd greatly prefer the party stay together whenever possible. Also I can't garuntee that every possible scene and adventure will be geared perfectly equally to each player's specialities,

This may not end up being an advanced game, I might shift it over to Casual as I personally don't like advanced all that much and it ends up being a barrier to many potential players. 

If the players decide to elect a leader amongst themselves that is up to them. I would say it's usually a good idea, and something I tend to encourage in my games, especially for really minor decisions that just need quick responses. As long as the player in question knows they still have to get their groups opinion for larger decisions, the group is ok with the decision, and the elected nob isn't being a dick. And by definition any ork if they were placed in charge they would become a nob.