Are all of the achievements in Elder Scrolls: Skyrim able to be acquired in a single playthrough, or will I have to save at strategic times to be able to step back to earlier points?
I'm assuming that if it's anything like Oblivion, that you are able to join multiple guilds one after another and complete their questlines and move to another.
Best Answer
There are a few achievements tied to the main quest which have you joining either the Stormcloaks OR the Imperial Legion, but these are awarded for picking either path, rather than siding with one group over the other (as in Dragon Age: Origins, for instance).
All of these achievements should be attainable in a single playthrough: