That sounds great. Nothing like a three generation ride.

While I started riding at 17 with a 650 BSA Lightning, that was a mistake and I went to a street legal dirt bike and I credit dirt riding with my motorcycle riding skills.
There were no MSF (motorcycle safety foundation) training courses then, and no separate motorcycle drivers license endorsement either. When I showed up to register my Honda CB750 at my first Air Force base, they wanted to see my MSF certificate and I didn't have one. They told me I would not be allowed to ride on base, and would have to push my bike to the gate (several miles). So I took the next available MSF course on base, and passed (I'd then been riding about 17 years).
There were no little 125/250cc bikes provided, you had to take it on your own bike. I can ride my Valks slow and balanced pretty darn well, but I wouldn't enjoy spending all day on one inside the little MSF box.