Since you guys have been so helpful, I've decided to throw this mishmash together to see if we can harmonize on a plan. So without further ado...
The current geopolitical situations concerning Tamriel and surrounding landmasses as of 2E:3745 PART I: THE MAJOR PLAYERS
High Rock (That's me!)
All things considered, doing pretty well. Had a couple of "Theological Differences" with the assorted Hammerfell Kings. Current strategy is warlording Skyrim. The major threats right now seem to be Skaven and...
Valenwood (DAMN HIPPIES)
Seriously, these guys! About as expansionist as the Thalmor, the Bosmeri have been busy in the last century or so. The former Kingdom of Falinesti has completely smashed Anvil and Rihad and are currently on a conquer lull. I suspect that they'll move on Kvatch and Skingrad next.
Cyrodiil
Currently split between the Colovians, Nibenay, The Heartlands, and Kvatch-Skingrad; Cyrodiil is pretty stable as compared to other games I've played, nevermind the looming Bosmeri threat to the west.
Skyrim
As you can see, the Colovian Estates have a pretty powerbase in the East, however the Rift does seem hungry for her de-jure lands back. The Kingdom of the Hjaalmarch has been on a conquer streak too, smashing Solitude and what was left of Whiterun. My current goal is the Reach.
So that's it, any feedback?