I assume you're referring to the Civil War, of which there's countless threads dissecting the problems within both sides.
But this is an interesting thread of thought nevertheless. I rather like the idea of actually drawing a salary based on rank as a soldier in the local army/militia. Even if the quest design is fundamentally the same (Go to dungeon, kill target) you can really create a unique identity within a faction outside of the quest using ideas like this.
On the whole, factions in Skyrim are kind of shoehorned in. Usually they have one phenomenally good idea within, that never really carries the guild past its weaknesses. The Dark Brotherhood fares the best of course so isn't particularly applicable.
Within the companions you have the sense of provenance that comes with the History of Skyrim. But it's squandered very quickly.
Within the Civil War, you've got the conquest/liberation/reunification going as you capture forts.
Thieves Guild has the revival of the guild itself, and the only time when becoming "Master" feels meaningful.
College of Winterhold has one of the best quests/tutorials ever, and if they had carried that model to more instances, it would have sold the "College" aspect. (The Ward tutorial, did anyone else actually learn how to use wards from that like I did?)