Well, ducatirdr, I'll be 50 in less than 3 years and I think my story is pretty similar to yours. You can read my intro (just posted yesterday) here
I also have a Harley and a Ducati, V-Rod and 999 respectively. I also recently bought an SV650 for racing in the lightweight class. I just got my first taste of Grom and like most, it makes me feel like I did riding my neighbor's minibike when I was a kid... smiles for days!
I bought my first motorcycle in my early 20's when I lived in Los Angeles so I could cut my commute down splitting lanes. I bought a Yamaha Seca II in about 91 or 92 and rode the Crest Hwy whenever I could make the time. It was stolen after a few years and I didn't have a bike again until reaching my 40's when I got the V-Rod.
Already into track events (HPDE) with a Boxster, I was easily drawn to track events with a bike, even though I was already in my mid-40's. So, there's the 999. After doing a couple of years of track days I realized that I was faster than most guys out there, regardless of age, and a friend convinced me that I should race. After some tough listening from track coaches, I finally resisted the temptation to buy a 2015 R1 and get the SV instead, with the intention of working on my skills a greater rate, as opposed to being seduced by the horsepower and gee-whiz tech of the R1. So I dove into club racing with the SV in the lightweight class (came in 1st place in my first amateur race last month). I knew my racing coach worked out with a Grom so I signed up to have a Grom training session with him and BOOM!... I'm hooked.
I've had the back end of my 999 step out on the track at speed and those fleeting moments are always good learning experiences. But being able to throw a Grom around a parking lot is priceless!
And yes, I am now totally interested in learning how to wheelie the Grom (even though I've never wheelied a motorcycle before). And stoppie and whatever other shenanigans present themselves! My racing coach began his professional motorcycle career as a stunt rider, so I'm sure I can get some good direction on the basics. Now I just need a Grom of my own...
Training on my buddy's Grom last Sunday...
Other pics attached of my V-Rod and tracking my 999 at Laguna Seca last June...