These are really good shots but I think Raido is on the wrong side of the Civil War!
I switched up on my restart as I hadn't done a play-through on the imperial side. All my other times I had either been Stormcloak or pretty much ignored the CW quests as much as possible.
Story-wise, he has his reasons why the imperial side would make more sense, most notably the closer proximity to the Thalmor whom he doesn't really care for all that much as they were responsible for his parents' deaths and later on his brother's too. I also wanted to see what it was like actually not going against Balgruuf for a change as I've always thought him one of the better Jarls, and one of the few that actually decides actions based on what it does for his people. In the past I always weighed that against giving Maven power over Riften, but in reality she had that anyway with or without the title as LLG is just an idiot. Looking at the other leadership changes, I think the people in more holds are better w/ the imperial option as Jarl than the alternative or are at least jus exchange nearly equivalent Jarls.
To be perfectly honest though, both sides really deserve to get their asses kicked more than just a little bit. I'd really prefer the negotiated end you can get through 'Season Unending' but ultimately that just prolongs the war longer, prolonging suffering and helping the Thalmor position as much as possible. As a result, whatever side I choose in the war (if my character is involved in it,) I tend to blow through the CW quest as quickly as possible.