If you join a side, the Empire is the least retarded one. Stormcloaks are basically MAGAtards, and their war is going to make the empire more vulnerable to the Thalmor, which are the bigger imperial threat. If you support anybody it needs to be critical support for the Empire as national liberation so the elves don't conquer the humans. The most based option however is to join neither side. The edgelord option is to join the Empire to pwn the Stormcloaks and then assassinating the Emperor, which would plunge Skyrim into even more chaos and effectively ensure Thalmor domination.
They're mercs but they tend to go for soft targets, and they have overwhelming force on their side compared to normal citizens. They're cops.
The only people with a political theory to speak of, but they go full cynic/nihilst with it. Basically vulgar egoists. The illegalism is largely justified, but they don't bother to try really changing things when they definitely have the pull to do so.
They're serial killers crossed with doomsday cultists. The only sane option is to destroy them, and killing Grelod to start the quest is so 100% justified that you will catch no shit from it from anybody in the entire game. If you play the game without destroying them, you are a failure at being a hero to the people of Skyrim.
>College of Winterhold
The main plot is pretty lame 2deep4u shit, but collecting lost books for Urag could actually make a difference to the world by holding back the decay inherent to the TES universe.
Since capitalists are metaphorically vampires, and vampires function a lot like porkies, the Dawnguard are automatically based for fighting them. Possibly the closest to genuine pure heroes in the entire TES lore. The Vigilants of Stendarr are too autistic about opposing daedra in contrast.
Dragonborn are automatically more or less on each others' level, so Miraak gets some credit for sending the cultists to kill you the moment he discovers you (assuming you visit the Greybeards right off). Bethesda could have put a little effort into the quest depending on your progress in the rest of the game. Maybe if you'd already beat Alduin and slain the dragon priests and such, Miraak might think twice about sending some cultists to merk you and then waiting for you to trample through Apocrypha before coming to merk him back. Pretty pathetic for such a dragonborn who's lived for ages in the realm of forbidden knowledge.
Pretty cool guys, regularly burn the effigy of a king. They also have a poem that each of them contributes to in turn as part of their career which is pretty commie.
Absolute trash, eat shit and die. Worse than the Dark Brotherhood. Useless cunts to the max. They just want a strongman to tell them what to do, but when they finally get you they do nothing but fuck with you, and worst of all they are central to the main plot, so you have to put up with their shit if you want to save the world. They have little to offer but insist on inserting themselves and extorting the hero into making them relevant, and they play LARPy spy games when the Dragonborn could just roll the Thalmor Embassy or sneak in alone. They are pure adventurist thrill seekers claiming to be true to your cause but constantly getting in the way. Demanding you kill Paarthurnax is the apotheosis of their autism. At least you have the option to recruit people who aren't shit so that canonically you can oust the original turds and fix the organization if you want.