Ok, it's been a few years since i've played, but I'm getting the urge because of Skyrim coming out soon. I've made numerous characters in the past of various types... blade guy, blunt guy, archer and mage. Each of them completed one guild or the main quest and none of them made it to a very high level. Also, I've never found any really awesome loot or weapon like Umbra or duskfang. What does everyone here suggest I should do with a new character? What weapons or armor should I try to find at a low level vs which ones should I wait until I'm a high level? Any ideas or descriptions of things you've done are welcomed and appreciated.

Also, one of the reasons i've never really used enchanted items is because the soul gem/ absorb souls thing to recharge them always confused and intimidated me. Do most people always fight with them or saved them for special/tough fights?

Chainmail is easiest to get at a low level if you go light armor. Do the "Order of the Virtuous Blood" quest and you loot Seridur's body for it.

Chainmail... check. Thanks

The best advice I can give to anyone playing Oblivion is to just raid Crayfish Cave. You may have to check the UESP for the location, but I think it's along the south of The Reed River, the one south of Cheydinhal.
It's a big cavern with several areas and plenty of chests. If you're lucky you'll find plenty of loot and get to slice your way through a fair amount of mythical creatures too.

Enchanted weapons (especially ones you make yourself at the enchanting altars) are great, and not hard to keep charged. To enchance success, I recommend:

Learn how to repair enchanted weapons by achieving 50 skill in armorer.
Complete Azura's Daedric Shrine quest (available at level 2) to obtain a reusable grand soul gem.
Join the mages guild and earn access to the University (enchanting & spell altars - woohoo!), even if you progress no further in that guild.
Learn spells that have the effects you might want to place on a weapon (oh, like shock damage and, for sure, soul trap).
Get your hands on a filled soul gem - the bigger the soul the better.
Get your hands on a good unenchanted weapon and enchant it with damage + soul trap so it can help you kill, while capturing souls to recharge.