UPDATE: NEWGUIDE NEWGUIDE NEWGUIDE!
Vital iPhone stats for this post:
iPhone version: 3G (should work with 2G and 3GS)
iPhone OS version: 3.0 (rock the hizzouse!)
Jailbreak status: Jailbroken using Pwnage Tool.
The Goal: Get live on-device XCode debugging without being a paying ADC member. This time OS 3.0 style.