I have done it! I have deviced the perfect plan for experiencing all of Skyrim's major questlines in two playthroughs. This should keep me busy for the next three months.
Archer with some magic support
Areas: The Reach, Falkreath Hold, The Rift, Eastmarch
Factions: Thieves Guild + Dark Brotherhood + Volkihar Vampire Clan + Imperial Legion
Home: Lakeview Manor in Falkreath Hold
Heavy warrior with some magic support
Areas: Haafingar, Hjaalmarch, The Pale, Winterhold
Factions: Companions + College of Winterhold + Dawnguard + Stormcloaks
Home: Heljarchen Hall in The Pale
After I've completed either character I suppose I could try and see how viable a pure mage is.