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I did it on a BMW R1100GS. 5 days, 22 hours and 43 minutes. IBA Sanctioned. Would I do it again, I would answer no, I have no desire to do it again.
As for prep, just make sure your bike is in good running condition, be prepared to ride in mud, dirt and gravel. If I was to do in on a C-10 I would invest in some front and rear highway bars. I do not think the C-10 is the best bike for this ride because of all the gravel, dirt and mud, but I know it could do it because I saw several Harleys riding the Haul road and they made it.
I've watched a bunch of Rick's videos. He rides through some pretty rough stuff on a C10. He's seen some wonderful sites, but to say it is a challenge, I think, is an understatement. Best of luck to anyone that attempts rides like that. Hats off to them and those that complete it.
I know several riders who have done this, and I would seriously consider renting a 250cc in AK for the haul road ride. Way cheaper than all the damage/wear and tear the Connie will get, and it's way easier to pick up. HTH.