My observing journey started in the 70s when my dad bought me the classic cheap 60mm refractor. I wanted to see the Ring Nebula with it, but I'm not sure that I ever succeeded. I spent a couple of years in grad school in astronomy before deciding that being a software engineer was a much easier way to make a living.
After years of drifting away from it, I picked up observing again about 15 years ago. I bought a used 10" Dob, then sold it and bought an Orion 10" Dob that had the Intelliscope object locator. I moved up to a 14" Dob, but when the encoders failed I sold it and got an Obsession 18" Ultra Compact, which has the biggest mirror I can carry. I also bought shares in the Goldendale Sky Village, an astronomy co-op that has some land in a Bortle 2 location, about 4 hours drive from my home.
My favorite thing to observe is galaxies, and with an 18" at a dark sky site, there is lots to see. It's pretty awesome to read about a 12th magnitude galaxy and know that I can observe it......