I'm curious how others do this when you start a new game. I'm a sneak so light armor is key, but the question is, do I bother learning Smithing early on and build my own set of crappy leather, or just pick up what I can, as I go until later in the game when the armor is more important?

Basically this is a question of early game, do you focus on fighting skills or trade skills, or some exotic blend? One of the first things I do is steal an Elven bow so I don't have to worry about having a decent weapon. But what of armor?

It depends on the character. I roleplay so nearly everything that happens in my games is determined by my characters.

Many of my armor-wearing characters take up Smithing right away. I generally roleplay characters with backgrounds, who entered Skyrim knowing certain skills. If they are accustomed to wearing armor, then many of them, it stands to reason, will have gained some knowledge over the years about how to make or repair it.

Well I think that's why Hide and Leather don't need perks.