Eoroch’s Guide to a Successful Oblivion Run
First off, look at this link:Â Â http://en.uesp.net/wiki/Oblivion:Quest_Timing
I am following a lot of recommendations on this for an early start. My personal recommendation is to not sleep at all while doing these, don’t turn in the “The Killing Field” quest, and make sure to do as much of the Arena line as possible (the gold will allow you to get a house - something I like to get early on to store items).
Good stuff to start next would be the Thieves Guild line (partly because I find it a bit boring at first, partly for the gold), and the Dark Brotherhood (this second because it gives you more rewards and all). I recommend doing this before the pilgrimage, so you can wear the KotN armor with no worry for your infamy increasing. Additionally, having the KotN armor will make the main quest line much easier.
Final tip: do not start with Shivering Isles!!! Everything else will seem boring by comparison, you will get what could be the best sword in the game way too early, etc. Besides the fact that it is the canon ending for the game :P
