Why should the best loot have the best locks? People value their possesions differently. Example: I live in a small flat in a bad street but I have two deadbolts a chain and a lock. If you broke in you would find a couple of guitars, a nice tv and a Ps3 and that's pretty much it that's worth cash value (A lot of my possesions are sentimental like books, personal writing etc.) now I know the need to have good security in a bad neighbourhood, but I really don't have much worth stealing so why secure it? Cause it means something to me.
This brings a bit of realism to the game. I don't want to know for sure that if I use a pick on a 'novice' chest that I won't find anything of value. It's nice to crack a novice and find a nice sword. It's equally disheartening to crack a master lock and find cloth and a carrot. But it's realistic and fits with the world.
I like this, and I agree. In the same spirit, I once used 45 lockpicks to free a prisoner in a cage. I got no reward at all, but it's what my character would have done if they were real. I like it when Skyrim feels like a real place, and not like a predictable game where risk=reward.
When you play Pokemon, you go into a tough dungeon knowing you'll get something good. If you play Zelda, you fight a tough boss knowing you'll get a great reward. Most of the time you even know what the reward is, without having played the game before.
Those games are fun, sure, but when i want to play like that I'll play one of them. When I want to feel like I'm getting lost inside a real place... I play Skyrim.