If you didn't have to work anymore...

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Gold wing for road trips across North America.
Trick KTM enduro for African and Australia adventure.
Duc or KTM race bike, do all pro6 bogie events each season.
Hunting and fishing often.
That would do it
 
Buy some land, build a small, efficient home with a fairly large shop.
Custom build my race rig, spend summers racing MX, winters doing snocross.

Bike line up would be a pair of 2 new yz250fs.
XR1200R
Triumph Tiger in that cool green they have.
And some form of hooligan supermoto style... Maybe the new superduke.

My Trans Am would be finished... 600HP "sleeper".

And start up my business ahead of schedule, which is something that won't feel like a job anyways. It's in the works, I'm just getting things lined up.
 
I dont want to retire but if I did I would own these...

04' zx10r
98' 916
92' zx7r
90' rz350

94' 993 gt2
82' 911 sc
90' Mustang Notchback

All I would do is work on my bikes and cars and try not to lose my license.
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