I'm trying this now and having a blast so far. My hope is that this is the character I'll finally break level 30 with... and maybe even get higher than that.
Classic Rogues tend to have limited proficiency with weapons, but lots of non combat skills and an ability to hit hard from stealth. I am making use of the following skills to reflect that:
One-handed - I'm not perking this out very much, but I'll grab a few levels of Armsman, probably Fighting Stance, and probably also the dual-wield perks. So far I've been using a single sword, but I plan to eventually dual-wield sword&dagger, or use dual daggers for stealth. I will continue to use just a single sword for blocking (see Block, below).
Archery - This will get more perk investment than One-handed. I haven't decided yet exactly how far to go here, though, or which side of the tree I'll focus on.
Block - This is taken for one reason only: Quick Reflexes. I'll get Block up to 30, take that perk, and then have a way to simulate the "Tumble" or "Acrobatics" skill by being able to dodge out of the way of power attacks. Obviously if I'm dual-wielding this won't help, but I plan to revert to single-sword when faced with hard-hitting 2-hander enemies, trigger Quick Reflexes, dance around behind them, and deliver a free hit or two. We'll see how it works out.
On the other hand, I may want to progress up the right hand side of the tree for things like Disarming Bash.
Light Armor - Rogues are traditionally proficient with this, so I'll perk it out. But it is a slow leveler, so may require training.
Sneak - obviously perk this out. Grab everything in the tree.
Pickpocket - I'll want to play with this, so I plan to take a lot of perks here. Particularly Misdirection, to steal equipped weapons. Never done it before, and the skill is an iconic rogue ability.
Lockpick - I'll work this up, and may perk it up to Treasure Hunter, but more for RP reasons than utility.
Speech - I haven't quite decided here. On one hand the merchant-side perks are appealing, but on the other hand I'll have fences through the TG questline.
Alchemy - definitely plan to perk this up to Concentrated Poison, but no farther.
So, no smithing or enchanting, and no magic whatsoever. I guess Enchanting may level a little bit if I end up getting magic gear and recharging it.
So, some questions:
1.) I want to simulate the classic rogue style of avoiding head-on confrontation, so I think I'll need to keep my Health fairly low. Since I'll be playing on Adept, what is a good level of Health, or ratio of Health to Stamina? Currently at level 10, Health is 130; Stamina is 150. I figured I'd keep Stamina several levels ahead of Health, but I'm not sure how far.
2.) I want the Light Armor skill to somewhat compensate for low Health, but since I'm not improving my gear it's not going to be easy. How do the high-level Light Armor perks play? Do they seem useful?
I guess that's it for now, aside from any comments you might have.