Who here dual wields on Master? Specifically, anyone dual wield with roleplaying restrictions? On my character I don't use smithing, so I don't overpower my weapons and armor. I know how tough Master is as I played on Master with a sword and board warrior. Seems like I will take a massive beating dual wielding and not being able to block. I know I need to use the sneak attack damage multipliers, and also use my bow, but for the first several levels is the secret to go around killing easy stuff until you can unlock these perks?

Level up heavy armor asap, and you're good. The damage you deal is redonculous(lol) and it barely matters what weapon you are using. I sword n' board and dual wield on my newest character, depending on the situation, and when I'm facing a particularly strong enemy, dual wielding is a Godsend. I did invest in smithing, but I only use nord hero weapons, and I dont stack with potions or enchantments to make the smithing better. Still doing buku damage.

I've already started using light armor... I am a thief/assassin character. Is that going to be a big issue?

Not really. Light armor still protects well fully upgraded, and is advantageous early on, since you can move around faster. Also, get become ethereal soon too. Very useful for dual wielders.

Not at all, any armor can reach the cap with the proper perks.

with dark brotherhood gloves you one shot most non-boss enemies even on master.

Light armor isnt a problem also, because when you're dual power striking, you stun lock the crap out of your enemies, so a lot of the time they wont get hits on you anyway.