* Having the Cyrodiilic Empire encompass High Rock, Solstheim and Skyrim by default makes little sense in the Second Era, certainly, since you end up with awkward things like King Jorunn be(com)ing an Elder Councillor.
* Has there even been an actual High King of Cyrodiil? I thought I recalled Titus Mede I being a high king in Cyrodiil before becoming Emperor, but I checked and apparently he was just a king. Honestly, I'd split the High Kingdom of Cyrodiil into Nibenay, Colovia, the Heartlands and maybe Bruma. Maybe have a decision to form the High Kingdom for someone who has both Nibenay and Colovia.
* The de-jure set-up in Skyrim is weird in so many ways. So I'll go by hold:
** Eastmarch is the most egregious offender, and stretches too far in almost every direction. Valtheim should be in Whiterun Hold (maybe with slightly adjusted borders). At least half of the Gallowrock province should be in The Pale, one way or another. Falkhammer should be in The Rift, and Shorstone should be where Ansilvund is. Might be a good idea to scrap the Eastmarch province and put Ansilvund roughly in it's place. Judging by TESV, Shorflow, Coldwinter (if you made it more coastal and not extend as far inland) and possibly Bleakrock (just because it would make greater geographical sense) should be part of Winterhold, not Eastmarch, since everything north of Traitor's Post and north-east of Windhelm is actually part of Winterhold.
** The Rift is mostly ok, although the north-west border of Ivarstead/Snowgrad with Hrothgar/Guldun should be more gently sloping than the sharp 45 degree angle it has now.
** Speaking of Hrothgar, what's the point of the barrier between it and every province but Ivarstead? It'd make sense if it was an ownable, traversable province like any other, but currently it just stops Whiterun having it's name stretch over it, which would make sense since the whole mountain is in Whiterun Hold despite the only way up being on the other side near Ivarstead.
** The Dawnstar/Frostflow border is too far west. Compare the in-game border with the Natalie Dravarol map; the border should be just to the west of Yngvild Island, and recede sharply westwards to the south. Most of the Ironbind province is actually in The Pale. I'd maybe have a Nightgate/Heljarchen province there that's part of Korvanjund, and merge Ironbind with Alftand. I'd also perhaps have Olenveld be a de-jure part of Roscrea rather than Winterhold. All that's ever been said about it in relation to Winterhold is how far away it is.
** Sunderstone juts too far into Whiterun. I'd maybe just get rid of or relocate the province of Skymarch somewhere else, then move Glenmoril and Sunderstone further south-west. Also, Brittleshin Pass is where Riverwood should be. I'd move the province further west and divide the old province between Riverwood and Helgen.
** Ravenhall juts too far east into Whiterun.
** The Duchy of Volskygge is...messy. Hraggstad is where Volskygge should be, Ustunhall is where Hraggstad should be. Hagsend should be a separate de-jure duchy; if a new province has to go where Volskygge is now, how about Darkfall/Mor Khazgur? Volkihar shouldn't be so close to Solitude, really it should be situated instead on the roundish island north of Northwatch that's currently part of Jehanna, with the current location of Volkihar island being part of Ravenscar or Coldstone.
** Highgate encroaches a bit too far into Hjaalmarch. Move the border just east of the little island north of the in-game location of Windstad Manor.
EDIT: A helpful illustration of Skyrim's new borders. Not perfect (especially the still squashed-looking Eastmarch) but better. The shaded red province is a new impassable Velothi Mountains province, mainly to smooth out the borders.

* Has there even been an actual High King of Cyrodiil? I thought I recalled Titus Mede I being a high king in Cyrodiil before becoming Emperor, but I checked and apparently he was just a king. Honestly, I'd split the High Kingdom of Cyrodiil into Nibenay, Colovia, the Heartlands and maybe Bruma. Maybe have a decision to form the High Kingdom for someone who has both Nibenay and Colovia.
* The de-jure set-up in Skyrim is weird in so many ways. So I'll go by hold:
** Eastmarch is the most egregious offender, and stretches too far in almost every direction. Valtheim should be in Whiterun Hold (maybe with slightly adjusted borders). At least half of the Gallowrock province should be in The Pale, one way or another. Falkhammer should be in The Rift, and Shorstone should be where Ansilvund is. Might be a good idea to scrap the Eastmarch province and put Ansilvund roughly in it's place. Judging by TESV, Shorflow, Coldwinter (if you made it more coastal and not extend as far inland) and possibly Bleakrock (just because it would make greater geographical sense) should be part of Winterhold, not Eastmarch, since everything north of Traitor's Post and north-east of Windhelm is actually part of Winterhold.
** The Rift is mostly ok, although the north-west border of Ivarstead/Snowgrad with Hrothgar/Guldun should be more gently sloping than the sharp 45 degree angle it has now.
** Speaking of Hrothgar, what's the point of the barrier between it and every province but Ivarstead? It'd make sense if it was an ownable, traversable province like any other, but currently it just stops Whiterun having it's name stretch over it, which would make sense since the whole mountain is in Whiterun Hold despite the only way up being on the other side near Ivarstead.
** The Dawnstar/Frostflow border is too far west. Compare the in-game border with the Natalie Dravarol map; the border should be just to the west of Yngvild Island, and recede sharply westwards to the south. Most of the Ironbind province is actually in The Pale. I'd maybe have a Nightgate/Heljarchen province there that's part of Korvanjund, and merge Ironbind with Alftand. I'd also perhaps have Olenveld be a de-jure part of Roscrea rather than Winterhold. All that's ever been said about it in relation to Winterhold is how far away it is.
** Sunderstone juts too far into Whiterun. I'd maybe just get rid of or relocate the province of Skymarch somewhere else, then move Glenmoril and Sunderstone further south-west. Also, Brittleshin Pass is where Riverwood should be. I'd move the province further west and divide the old province between Riverwood and Helgen.
** Ravenhall juts too far east into Whiterun.
** The Duchy of Volskygge is...messy. Hraggstad is where Volskygge should be, Ustunhall is where Hraggstad should be. Hagsend should be a separate de-jure duchy; if a new province has to go where Volskygge is now, how about Darkfall/Mor Khazgur? Volkihar shouldn't be so close to Solitude, really it should be situated instead on the roundish island north of Northwatch that's currently part of Jehanna, with the current location of Volkihar island being part of Ravenscar or Coldstone.
** Highgate encroaches a bit too far into Hjaalmarch. Move the border just east of the little island north of the in-game location of Windstad Manor.
EDIT: A helpful illustration of Skyrim's new borders. Not perfect (especially the still squashed-looking Eastmarch) but better. The shaded red province is a new impassable Velothi Mountains province, mainly to smooth out the borders.

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