My character on Skyrim is constantly overloaded. I'm paranoid about putting anything in a chest, because I did that a few times in Oblivion and lost everything. I've got a bunch of Orcish armor sets, and other heavy crap that I'll never use (because I'm a thief) but I can't bear to throw it away, or sell it for a fraction of what it's worth.

I'm the leader of the thieves guild, so I'm able to sell stuff at about 1500g a time. There also a few fairly wealthy vampire vendors in Castle Volkihar, which I've been unloading stuff too as well.

I did the Stones of Barenziah quest, so I've got more jewels, gems, and precious stones that I know what to do with. I've got hundreds of gems, and I gotta sell them like 5 and 6 at a time because NOBODY IN SKYRIM HAS ANY MONEY - I've been reduced to selling things to my own wife, but she's only packin 750g at a time.

I didn't level my speechcraft, so I can't invest in merchants... and I'm not interested in cheating, or using a 3rd party mod. How am I supposed to lighten my load and turn some of this crap into money? I'm still trying to get the money achievement, and furnish 2 more hearthfire homes.

Somebody wanna help me out here?

Sounds like you have OCL (Obsessive Compulsive Looter). I knew a few people who suffered from this condition when I played MMO's.

My suggestion would be to stop looting all objects besides gemstones and base / enchanted jewelry. Pound for pound, you'll get more money out of those items per weight than anything else (no pun intended), plus they don't overburden your character with encumbrance. Sell what you can and keep the rest for the next merchant shop / stall.