Hey everybody, just put together a new PC and have some great mods and I'm looking to really challenge myself on master difficulty playing as an assassin. First, here are a few of the mods that I got:

Path of Shadows: Stealth overhaul, reworks the majority of the stealth tree. Removes the broken abilities of silence and shadow warrior, beefs up on some other abilities. Highly recommend this to anybody else playing stealth. http://skyrim.nexusmods.com/downloads/file.php?id=10456

ACE Overhaul: Changes a bunch of the perk trees and how combat works. Makes them synergize with each other as well. Archery tree rework is fantastic http://skyrim.nexusmods.com/downloads/file.php?id=10037

Dual Wield-Parrying: Just what it says, allows you to parry while dual wielding. Normally I'd use this with deadly combat, but I'm not sure if DC is compatible with ACE (both change some combat features) so I'm not going to use it. If it feels too OP I'll drop it I guess.

And some other well known mods, such as Occupy Skyrim, Deadly Dragons, Dragons Diversified and Warzones: Civil Unrest so the land isn't quite as boring as it normally would be.

Sneak and One-Handed will be the main 2 priorities, but then I get a bit stuck. I plan on using a bow quite a bit, and it's pretty much a necessity with Deadly Dragons and Dragons Diversified. But I'm not sure whether I should stress archery or a crafting skill as being more important, I'm going to need one of alchemy, smithing or enchanting to succeed (leaning alchemy, it just fits assassins so well, but I'm up for any crafting skill that's suggested).

My biggest question is, what ratio of Health to Stamina to use? With deadly dragons on master, the dragons just hit so damn hard (especially early on) that if you get caught in an open area with no cover you are sorta screwed. But without enough stamina to chain power attacks, many NPCs besides dragons become a royal pain.

IDK how much the mods matter in the decision (I'm on PS3 playing on Adept) and I went with probably 2:1 or 2:1.25 Health:Stamina - I don't have the game on, but I think I may be around 500/300 Health/Stamina. If you didn't know: daggers use so little Stamina for power attacks it's almost like a bug. I primarily use Stamina for carrying weight.

Excellent choice for mods. Deadly Combat, Path of Shadows and ACE are all ridiculously good. I find the dual-wield parrying thing to be a bit overpowered with Deadly Combat as the damage of dual wielding power attacks with fortify enchants becomes so sick in the end, the tradeoff of not being able to block seems somewhat fair.

Also, there's a good mod called Two-handed Rebalance if you want to do more of a ranger-type character, fits in very well with the Path of Shadows, allowing 2h sneak attacks to deal some real damage later on when your sneaking is high enough to allow you to get close.
http://skyrim.nexusmods.com/downloads/file.php?id=11159

I'm doing a sneak/archery/two-handed/alchemy playthrough right now similar to yours. I'd suggest focusing heavily on Bows early on as you're slowly skilling up Stealth and unlocking dragons only after you get the Shrouded Hood (+30% fortify archery) and Gauntlets of the Old Gods (+20% fortify archery) and a fortify archery neck and ring. You also get a Forsworn Bow, which has a pertty amazing damage range, although the mismatching system might give Imperial Bow a slight edge.

I dump all points in stamina for this build. More carry weight, and as long as you pick off the weaklings with bow off stealth and do good timed blocking against the more durable ones, anywhere between 100-200 health seems alright.

Thanks for the advice. Based on your response I'm assuming deadly combat and ACE don't interfere with each other? I know ACE has a few slight changes to combat, but I'm guessing deadly combat might just overwrite them. I'd really love to be able to use both of them together. I'll take a look at two-handed rebalance, though TBH I much prefer 1H on this type of character. Definitely does look great for a archer/ranger though.

As for dual wield blocking, I don't plan on leveling enchanting much- in fact I've not really made a character yet where I've gone deep into the enchanting tree. I just really love alchemy I guess. So I'm not sure how strong of a +1h damage enchant I can get on the 1h weapons, and I'm not a fan of the fortify skill potions (I think ACE fixes fortify pots somewhat, if I'm not mistaken?). So to me it seems like somewhat of a necessity, but I could be wrong. I've done master playthroughs before, but that was before overhaul mods were released.

It's a pretty significant difference in terms of challenge (btw if your PC can handle it, I can't recommend this game for PC enough! Mods turn it from great to epic). The only problem with stacking health on master is that no matter what, the NPCS just hit so damn hard that you HAVE to be able to cut them down ASAP especially if it's a crowd.

Yeah, the mods sound great and I probably have one PC around here that could run Skyrim on low graphics, but I got tired of chasing hardware upgrades and having a bunch of decent and good components laying around because I kept removing them for great components.

I only play on Adept, but I improve my armor past the cap...even on my sneak-type - just in case.