Or is it gonna be rough without the best gear?

Part of the fun of the game is finding loot. Smithing always seemed boring to me

of course you can, sneak makes it really easy for players to never get hit at all.
the only difference gear is gonna make is you'll be even less inclined to get into range of enemies and kills will take longer.

What? Sort of obvious that you can. Why does having smithing make it any easier?

Dark Brotherhood gloves + Assassin Blade perk = Win.

If anyone knows about how to kill people effectively, it's this guy (judging by the avatar anyway).

But seriously, that combination will pretty much wreck anything you come across.