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Good Luck with the journey. Honda hasn't changed the basic design for their 4 strokes from back in the early 70s, starting with the CL/SL/XL/XR and now CRFs for a reason...good design. Simple maintainence and they are bullet proof.
From a guy who's done this...don't buy them new. One summer, I tried to get my wife into riding, and she was all for it. We bought all the gear, a trailer, and two race dirt bikes. A Yamaha YZ-450F for me, and a Honda CRF-150R for her.
The next year, I sold it all, for a fraction of what I paid, and everything was essentially brand new.
This time of year, I'd be saving pennies, and looking at Craigslist. I'm almost certain you can find something that isn't brand new and will meet your needs.
definitely worth it. My dad bought me a honda XR100 when i was 12 or so and i haven't looked back. one of the things i will always remember fondly about my dad was him teaching me to ride it... an experience for the ages for sure. I would not be riding a harley now if it weren't for him. He hung up his riding days when he had kids and never regretted it. Now im 25 and were both on harleys.
My first love is the dirt, sorry guys, NO HD could ever replace the years I spent on those bikes. The bond I developed with my Dad became very very strong during that time. In your shoes I wouldn't even bat an eye at getting the dirt bikes, if I could keep the HD I would, but there wouldn't even be a second thought if I needed to sell it, poof gone.
Sell the Harley, buy the motocross used, hopefully have enough left over to buy a used HD that needs wrenching and everyone gets to know how to ride, and also how to wrench... Memories are made of this.
I am going to be the odd duck and suggest something "OK used" - a couple that maybe need work. My dad didn't ride but I got the bug young; say 6 or so. He picked up an old 125 that needed some work and we worked on it together - him learning while he was teaching me. I went a little nuts from there and was doing total rebuilds by the time I was 10 and he hung back a little and stayed basic shade tree mechanic. But those times bending wrenches and talking about the universe and everything were fantastic in ways riding side by side couldn't be. A lot more bonding as I look back on it.
Oh and I will be the dissenter on used 4 stroke mx bikes, I wouldn't buy one cause I know how they get ridden and how they don't get taken care of. If it was a 2 stroke used, go for it they take nothing to fix but if something lets go on those bikes(4 valve CRF 250 450) it is usually fatal and expensive.
Buy a couple older ( cheap ) bikes that need a little fixing up. You will teach him a little about what makes a bike tick. He will also have a little more respect for the bike if he has actually done some wrenching on it. When you go shopping for the bikes make sure he is involved as well. I remember the time me and my old man went shopping and what he taught me. After 6 mos or so I was doing all the wrenching for the both of us. That was one of the few times I ever enjoyed with my father....
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