I wish I could forget everything about oblivion so I can play it again. lol.. I have almost 300 Hrs.
Start off with the Dark brotherhood questline, lots of people say its the best questline in the game. That way you can get your sneak skill up, which helps out alot when you travel to Oblivion. Plus you get a lot of useful equipment.
Also the Arena is fun to do "Gladiator style" fighting, but having decent equiptment would be a big plus. When you complete the Arena fights you will meet a guy called "the adoring fan" It is a fun pass-time among oblivion players to find new and inventive ways to get him killed. (he eventually comes back) I'm sure if you searched Adoring fan in youtube you would get piles of videos.
As for finding equipment, thats the problem, equipment and enemies are leveled with you. Which sucks, but what this means is as you level up they will to, to keep the game fair I suppose. Its kind of sad, because you don't get any "Oh **** run!!" moments. I used to play TES3 Morrowind and there was more than one time where I bumped into a tough enemy and had to leg it.
As for making money, carry as much stuff out of caves as you can. But if you do the dark brotherhood and thevies guild quests the only thing you will need money for is houses and furniture, because you will beable to break into shops and steal it.
For fun, I ususally try to pick off the "black horse courier" riders (people who ride on the trails delivering newspapers from the imperial city to other towns, evenditally they fly along on black horses with torches.) and trying not to get caught and get a bounty.
Killing the adoring fan never gets old....
Oh and to get people to fly through the air with spells you need one called "finger of the mountain". It's funny...