No need to root at all before hand. Following the QDLTool and Streak Upgrade guide tutorial's and getting the drivers and everything setup, all I did was run QDLTool to factory reset from Android 1.6 to 2.2. Once I did that it's as easy as flashing a recovery with Fastboot and then throwing a custom ROM on your SD card to flash.
I'm running StreakMod recovery with the Traveler DSC ROM.
Thanks all for the input/advice. I appreciate it.
PS: Someone thought I was a guy hehe, Sorry to correct but im definitely a girl! x