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Here's another vote for encouraging him to enroll in an MSF course. If he has the means, maybe he can also pick up a used Yamaha V Star or similar small cruiser and ride it for a couple of months and then unload it for what he paid for it.
I was him 10 years ago. Hadn't been on a bike in 20 years. I took the MFS course. I then ordered an 06' RKC. I had by buddy Dale pick it up with me. Dale road it to a local parking lot. I practiced there some slow speed maneuvers. Later that week we went to a state park. I practiced going up and down mountain hills and braking. Later on during the week my buddy Tommy came by and we took a 125 mile ride. Well now the RKC has 70K and I also have a 15' Limited with 6.2K.
You should help him. Explain your concerns while also encouraging him.
Remember experience is gained through riding and racking up the miles.
It was a 23 year gap when I was reintroduced to riding again. My brother offered me his Heritage to ride when I went to visit him in Florida, he has a Road King for himself. I really didn't realize how much I remembered about riding or how much I'd forgotten until I went for that first ride.( I think my brother was way more nerves than me.) That first day of riding really got some of my confidence back. The next day my brother asked if I would mind watching a video of riding instructions before we headed out for the day. I didn't mind, after all it was his bike and nothing to lose watching a video. The video was Ride like a Pro. After watching it I really learned just how much I not only forgot but just how much I never knew. I would recommend that to all who ride. Its a sad day when you can't learn something no matter how long you've been doing anything. Ride Safe.
My first bike was an Ultra, never ridden before, I took the riders edge course and did the break in miles at night with leas traffi . 85k miles later no incidents.
So yeah, help him, take him out and let him get use to it all over again. All of us were beginners at one point.
I know guys that have ridden "their whole life" that I wouldn't ride in a parking lot with, and I know guys that have ridden for a year that I would ride to Sturgis with. It just depends on the confidence and skill.
Just because he hasn't ridden much on a 800 pound bike doesn't mean he will suck at it, and vice versa...
The new touring bikes are easy to learn with, I never rode a touring bike before I picked it up in Texas. I was riding the dragon 2 days later on my way back to DC. I never got to practice on it because I flew in later than I planned.
Tell him to take it easy, and hope he isn't cocky and hard headed like me. My favorite line is "I got this!"
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