he is planning on a sell in theory when its 6 years old. 2002 model now 2008. So the next car he would in theory sell when it is six years old. The value of that ar will be equal or even less than today's value of the 2002. So again it comes back to today's cost difference of $17K.
He has alreday had some repairs to the 2002. Possibly to revisit those same repairs for the 2005.(CPO paid). Maint. is out of pocket and again, equal..both cars need to be maintaned.
I think this works?
but then again..we all just do what we want becaus we want it. ;-)

allroad FAQ SITE.
2003 allroad 6 speed manual w/165,000 miles as of November 2008
DRIVETRAIN:
• APR 5.0: 93 Octane
• Stratmosphere Hyperboost Diverter Valves
• Toy Guy Short Shifter
• AWE-Drive Train Stabilizer.
• HP-2 Caliper Reverse Mod
• ECS Slotted F & R Rotors
• PBR Metal Master Pads F&R
• ECS Stainless Brake Lines
SUSPENSION:
• Hotchkiss H-sport stabilizer bars F & R
• S4 Heavy Duty Tie Rod Ends Inner and Outer
• Borbet FS 17 x 8 Wheels with Falken Ziex 512 UHP-A/S
• RS6 Reps with Nokian WR UHP M/S
• HR 12MM Spacers F&R
• 402 mod down 20MM
INFOTAINMENT
• Kuda Cell Phone Mount w/hardwired DC plug.
• Parrot Blue Tooth Cell Phone/GPS Module
• Palm Treo 700 with Tom-Tom Navigation
• Ice+link Plus w/Mini Ipod
• Hardwired V-1
MISC:
• Audi OEM Trailer Hitch