That guy is a jerk. I wish we had more dialogue options when talking to him. I feel like he is bullying me ;_;

Spoiled Brat or a Crazy old man.

Falkreath is toast, just behind the Reach in the 'this Hold is screwed' contest.

What about Riften? your choices are Maven's puppet or Maven herself.

Riften is actually one of the better cities and one of the Holds in the best shape in Skyrim surprisingly:

Most racial diversity/racial equality

One of the largest businesses in Skyrim located here

Likely the fishing and hunting capital of the province

Potential to trade with both Cyrodiil and Morrowind

Good weather for crops/food production

The TG/Maven thing is obviously a mess but Riften is still relatively well off, note that I said relatively.

Funny how the two cities where Mer have the most power and economic success are both in Stormcloak Holds.

If you really want to remove him, you could join the Stormcloaks to get Dengeir back into power.
Then again, Riften and Windhelm are right next to Morrowind.

Riften and Windhelm are also home to the largest communities of (non-Thalmor affiliated) Altmer and Bosmer in Skyrim, if we go by what is presented in the game.

I don't care for Siddgeir either, mostly because he isn't a good leader (at least in my opinion). It's pretty obvious from dialogue in the game that he is lazy, because he leaves most of the "Jarl's duties" to his steward. Dengeir makes a much better leader than his nephew from my perspective.

Exactly. Kind of funny how Altmer are most successful in Windhelm and probably all around the most successful race in the city with all 4 owning businesses.