I feel like I'm gonna portray a character of my real self which isn't particularly accurate by saying this, but to hell with it.
It's amazing there is Insurance and NO Risk at such a cheap price. I'm not a millionaire, but there seems to be LOADS of people who are, who can just waltz around in ANY dungeon or situation, and come out of it unscathed with nothing lost. Even if you're not a millionaire, you can walk through a dungeon and die 3 or 4 times at least and not have to worry about your best Leather Gloves being lost, amongst other items of critical value - which for the love of god, shouldn't be able to stick to you throughout all the thick and thin.
Ironically, it seems to me the Newbies that have it worst, with so little Gold to begin with (Still 1000gp right?), and no way to protect their equipment which they need to progress their skills with, and survive as they take their first steps in the world. Talk about having it tough.
Suffice to say, auto-equipping just removes 30 seconds of hassle that I'd rather not dissapear; maybe I've been reading the DFO forums way too much, but dying, ressing and running straight back into battle even more prepared sounds like an Arcade game or something.
This is of course my opinion, that such an enhancement would only make things worse. I ponder what people would say if you had to drag EVERY item off your corpses again?