I think the best item to enchant is an exquisite ring. I know that clothing can enchant less, though daedric armour/weapons may be able to hold more enchantment than exquisite rings.
Yes, the lack of people with enough money to buy stuff is quite annoying. In Caldera, there is a scamp who has 5000 and doesn't adjust his prices (ie if an item says it's worth 4500, that's what he pays). There's also a sand crab with 10,000 down on a tiny island in the south (sorry, don't have my map handy - near a shop wreck). He's pretty inconvenient though, especially if you have a lot of heavy items to sell. If you have the tribunal expansion there are vendors there with a lot more money. And I believe there are plugins with rich merchants as well.
If you're still short on cash, you may have to scale down the item you're after. It's nice to have items with invisibility 100, but that might not be feasible
