Board Thread:Skyrim/@comment-120.28.157.86-20140406014559/@comment-86.29.86.229-20190915234950

I tend to go imperial when running a thief character. The ties the Thieves Guild has to the empire make it seem to mesh slightly better from an ideological stand point, increased corruption and most contracts leading to pro-imperial outcomes via helping their sympathizers gain power in some way, Maven being the main example of this connection but their are others too if you do some digging. Not surprising though considering the lore of the guild.

Depends what you're doing in your playthrough though, if you aren't bothering with the guild storyline, then could go in any direction really.