Here's mine, in order of ownership. I'd love to read about others' experiences.
Back in the late '90s I got my first anything with an engine, a fairly clapped out 50cc Yamaha Spy 2-stroke scooter. I was 16 and it was affordable transportation, but it lit the spark of interest in two-wheeled fun.
Then around 2002 I was in college and working part time, I sold the scooter and got a 1997 Yamaha Virago 125. My first 'real bike', with a thunderous 10 horsepower.
A couple of years later I graduated college and wound up getting a car to go to work in, as I lived in Ireland where it rains more often than not, and I could not afford nor have the space to keep the bike along with the car, so the Virago was sold.
Several years of 4-wheeled life pass by, then we arrive at 2014. During the previous 10 years I have moved to the US with my job, got married, and so forth. Now I'm old enough and financially solvent enough to afford a bike as well as a car and a place to live, and I go get my motorcycle endorsement (again, I essentially had to start over when I moved countries) and buy my first (and only) brand new bike - a white 2014 Suzuki v-Strom 650. I lived in Idaho at the time, which provided plenty of access to mountain roads and stuff to ride around on, it was a good fit. I kept the 'Strom until 2018 (I had recently moved to the flat midwest), and then started bike-hopping more.
I traded it in for a used and cheap (because they were very unpopular and wideley considered to be ugly) Honda CTX1300. I wanted to try something with a V4, and the OEM panniers and stuff were very attractive to me. I kept the CTX for just under a year, though. I just didn't fall in love with it. It was very comfortable and would be an excellent machine to ride across America in. Think of it as Goldwing lite. It felt a little bit too 'dad' for me at the time. Also it weighed like 725 lbs.
At the end of the season I traded again, this time getting myself onto a 2016 Yamaha XSR900. That bike was awesome. It had a torquey triple that could get going silly fast, with retro-influenced style. I rode the XSR for several years, and did some simple bolt-on mods like an improved LED headlight (the stock halogen was garbage), nice exhaust, better seat, etc.
I sold the XSR in spring of 2023 and bought a well-used 2014 BMW F800GT. It was a drop of about 30 horsepower from the XSR, but came with a lot of practicality, with OEM bags and stuff. However, this was another bike that I just didn't connect with, and I traded it in spring of 2024.
I replaced the BMW with a 2018 Triumph Tiger 1200 XRx with only 2,500 miles on it. It came with the expensive OEM panniers and is the first bike I've had with factory heated grips and seat. It also has gobs of power with that big triple, something I missed from the XSR. It doesn't get up and go quite like the XSR considering the extra weight and higher center of gravity, but it has more than enough power to keep me happy now. It also is a single-sided swingarm, shaft-drive setup which I think is pretty cool.
I still have that Triumph today, but a few weeks ago I acquired another bike - the 1975 Honda CB750F super sport pictured here. It has 34,000 miles and change on the odometer, but who knows how accurate that is. The state of Illinois doesn't require odometer readings for anything vintage. This is my first inline four bike, and I've been enjoying riding it around. It makes the 2018 Triumph feel like an absolute rocketship. I haven't hard carbs since that late '90s Virago!
The CB had 35-year-old hard-as-rock dry-rotted tires on it, but otherwise it ran pretty great. I've replaced the tires (that was a real pain in the ass, I don't think I want spoked wheels again on a future bike), and have tweaked a few things to make it run even better. Next job on the list is new brake pads and steel-braided lines. The front brake lines appear to be original from 1975 and they're spanked. Also, the front brake light switch is kaput. That's plumbed into the brake lines so I'll replace that when I do the lines.
It certainly helps to have a community of vintage bike nerds in the area to give advice, most shops do not want to work on anything this old.