Similar story for me. Grew up on used bicycles, and shortly after starting grad school in the early '90s I spent $600 on a pretty high-quality mountain bike. I spent the next six years riding like a demon: commuting, pleasure riding around town, trials-style riding (Madison’s Capitol police were not happy with me riding full-speed down the stairs), trail riding in Wisconsin state parks and in Michigan’s UP.
And then…
After I finished grad school, I bought my first motorcycle. A brand-new BMW, $16,000. It’s difficult to put into words how much bang I got out of my buck. I’ve written about it previously:
I used to have a bike like that, and I used to ride it like that. Custom saddle with backrest, barbacks, and a few other tweaks made it fit me perfectly, and after 130,000+ miles of riding it and wrenching on it I had grown intimately familiar with it. Took a trip from the upper Midwest to California, and several trips to the Rocky Mountains and the desert southwest. Track day. Saddlesore 1000. Every kind of weather, from “goddam it’s hot” to “WTF, it’s actually starting to snow.” I did feel that kind of unity; it was my horse. When I stopped somewhere for lunch, I’d sit where I could watch it - not for security reasons, but simply because I liked looking at it. And not just because it was pretty, but because looking at it brought up a ton of memories of all I had been through with it. For me, all of the scratches, dings and scars weren’t depreciation; they were a storybook, a historical record of all the adventures we had been on together.
I like my current bike - it’s more powerful, has cruise control and a heated seat and other things my old bike did not - but I have a much stronger emotional connection with my previous bike.