Alrighty! New thread means starting off with the grandiose idea of having a solid, directed discussion without tangents or distractions, which will quickly devolve into random 3 post conversations that flit back and forth with no rhyme or reason...
Starting off, I'd like to bring up Factions.
Generally speaking, Factions in TES have run the gamut from passable (Skyrims Thieves Guild) to atrocious (Oblivions Dark culty-hood). In my mind, however, their biggest failing has been in their conception, as opposed to their execution.
The various factions, particularly the big ones (the Guilds) have been based on gameplay archetypes, rather than adhering to their own in-universe presence. The Fighters Guild, for instance, has been portrayed as a purely physical organization, rather than the Mercenary regulatory body it is. It should welcome Mages just as surely as Knights and Barbarians. Even Mages need security, and there should be room in a mage organization (up to a point, anyway) for a bruiser. Bandits, pickpockets, extortionists, burglers, muggers... Al of these are thieves, and a criminal organization should represent that range.
Moving away from archetypes opens up more options for jobs (Radiant Quests) and character options, without forcing particular types of characters into particular factions.
I'll let that settle in a bit before I go on about faction reputation, blacklisting and questlines...