I originally posted this at http://www.uesp.net/wiki/Skyrim_talk:Enchanting#Ways_to_level_enchanting_and_to_make_profit_section but thought I would share it here.

A good way to level enchanting and make considerable profit is by collecting and enchanting clothing. Clothing weighs one pound and is practically everywhere. You can find clothing in end tables, on corpses and often multiples in dressers. You don't even have to engage in combat to get clothing since they are available in all towns free of charge without stealing. A side effect of this, which may be desired or undesirable, is that you do not level smithing. Cloth wearing mages benefit from this because they do not need smithing and increasing smithing will unnecessarily increase level, which is especially bad early on when playing on expert or master difficulty.

If you are a magician, the best location to trade your enchanted clothing and jewelry is the College of Winterhold. Find your skill trainer of choice, for instance if you want to train destruction, locate Faralda the destruction master trainer. All magic skill trainers, with the exception of enchanting, are also merchants. If you have lots of gold available, and want training, train first. This will add your gold for your training to the available gold she has. Then you can sell the large amounts of enchanted clothing and jewelry items or even unenchanted jewelry made from cheap iron ore changed to silver or gold with the alteration spell "transmute" which will pay for your training or spell books. Alternatively, the magic merchants will offer robes enchanted with magicka regen and reduced spell costs for the appropriate school, these tend to be expensive, especially early in the game when you are unable to enchant items to the same level of enchantment. You can even buy more empty soul gems or charged soul gems to train your enchanting skill or make more profit enchanting other items with petty gems. Better yet, you can trade your items to Enthir at the college in the hall of attainment for black soul gems, or daedra hearts for daedric item smithing.

Typically, only general store traders will buy jewelry or clothing, there is usually only one in each town and have around 750 gold by default. However, at the college in the hall of countenance, there are four, Phinis Gestor, Faralda, Collette Marchance, and Drevis Neloran who have 500 gold available each for a total of 2,000. Please note they may not all be there at the same time. This saves time having to fast travel or using the wait function.

Hope this helps!

A couple of good ideas there: Thanks for sharing your tips.

Joining the Dark Brotherhood and possessing the black star synergizes wonderfully. You accept a dark brotherhood contract to kill someone, trap their soul in the black star, take their belongings. You get gold for completing the contract and selling the victim's belongings that you enchanted with their own souls. It is also deliciously evil. >:3