I'm sure each person has their own stories. Here's mine:
Yes, I'm guilty of possessing several telescopes. I purchased 4 Galileoscopes when they first hit the market -- at $15 each plus shipping. Why 4? Well, they were remarkably inexpensive, and I thought I might want to pass some off to others as gifts at some point in time.
I received my first "serious" telescope on a Christmas morning -- probably in 1967 since I recall dating several of my earliest observations "1968". My next telescope (an 8-inch SCT), the first that I purchased myself, was purchased in 1977 -- yes, nearly 10 years later. My next telescope was purchased as parts that I assembled into a finished 10-inch reflector in maybe 1987 -- after another 10 years. Then my Astro-Physics 130mm apochromat arrived in 1995, give or take one year. From 1995 through the present point in time I added the previously mentioned Galileoscopes, an 80mm f/5 Short-Tube refractor as a "grab and go" telescope, a 12-inch reflector (to see what I was missing out on in the larger aperture department -- I concluded that I wasn't missing out on anything of any significance to me). My last telescope was purchased in 2015 -- because that was basically the telescope that I had really wanted back in 1995 (but no one made one back then) -- when I had decided to "compromise" by purchasing that 130mm Astro-Physics apochromat.
At least three other telescopes came to me as "freebees". One was won as a door-prize at a star party. The other two were discarded by their previous owners (and many would label those two as "department store trash telescopes" -- especially the one whose refracting objective was a "singlet" -- not even an achromat.
Out of all of those telescopes, the first one "vanished" after I left home to attend a university. The SCT got traded off for a couple of (TV Nagler) eyepieces at a star-party. All of the others I still have, even though I had offered to give away (free of charge) the 10-inch to a neighbor, but the neighbor never came to pick it up. So, I still have it.
I also have three binoculars that were purchased several years from one another -- an 8x42, a 20x80, and a 25x100 -- each very different from the others in aperture, magnification, and weight. Each having substantially different capabilities -- not a very extreme number of binoculars, if I do say so myself, considering the overall span of time.
I also happen to have the luxury of being in possession of two observatories and living under a "seriously dark" sky, but I now use only one of the observatories.
So, why so much stuff? It was accumulated from 1967 through the present day -- a nearly 60 year period of time with only two telescopes that have departed from my possession. My home, for the past 40 plus years, has been pretty much in the middle of nowhere. It's not easy to pass old telescopes on to others from such a location, and I find it difficult to take a telescope to the nearest dump. I mean, a telescope is a telescope. They deserve to continue to see light from various celestial bodies or at least remain lovingly stored until they can next do so.