Leveled or not leveled? I don't want to make the same mistake as I did with the Nightingale armor which I got at level 20, which has to be my favorite armor in the game. Also, what can I do to max out my Nightingale armor to legendary? I'm 100 in smithing, but I put all my perks in heavy armor for the daedric bow. Will this hurt me or do I need to put a perk in the light armor branch of the smithing tree somewhere? Thanks in advance.
I have both armors, and could answer your question if I understood it better. What do you mean leveled or not leveled? What does that mean.
None of the brotherhood armors are leveled the stats on them is what you get at any level.
It means the later you get it the better the base stats on the armor will be, the max being 50. At least from my understanding.
Not to my knowledge that doesn't happen, I got them rather close (maybe about 5 levels apart) and I don't know if that is big enough to make any difference. But I'm sure it isn't. So I'd say go for it! They aren't THAT good anyway, so even if it is, since you've got that smithing level your golden.
So should I just upgrade my Nightingale to Flawless (or Legendary, not sure which is higher) or am I better off the the Dark Brotherhood armor upgraded?
My character has 100 Illusion, so the full Nightengale armor really suited my playstyle. However the DB armor(chest part) is overrated, all it does is give you poison resistance which is useless, so always wear a different chest piece than DB. Even if it's the ancient one.