I think telescopes are like cars the cars of our youth. You get rid of them, and decades later you wish you had them. Why? Who knows. I started with some sort of Jason reflector and then moved to an Edmonds Scientific 4 inch reflector. I think a lot of astronomers of my generation had that reflector.
My Cave Optical 8 inch f/8 reflector was a wonderful telescope, and I knew it would be the last I'd ever need. I got it in 1966, and in 1968 I moved up to a 3 inch Questar. At the time, they were considered the best - the Rolls Royce of telescopes.
The Jason and Edmonds are long gone and nearly forgotten. The 8 inch is now property of Ware Shoals High School.
I still have the Questar. It is still better than any other instrument I've ever used. It's so portable.
I also have a 10 inch dob, which I like because it uses a 2" 32 mm eyepiece and that is easy on these eyes. It can use the 2" eyepiece or the 1.25" with the adaptors that come with it. That one travels well to star parties, but it is a bit bulky to use for just a few minutes of observing. For that I use the Questar.
To observe the sun, I have the Questar, but I also have one of Coronado's PST - Personal Solar Telescopes. Mine has an aperture of 40mm, so it is one of the smaller ones. Still, I can observe the sun in H-Alpha light and see the prominences and filiments and active regions of the sun.
I have a 85mm f/5.6 Apochromatic Refractor telescope, but I'm selling that one.
I also have a 14-inch f/5.5 Schmidt-Cassegrain but it is permentantly mounted at a dark site in Georgia.
So, how many telescopes does one person need? Just one more.
With this being the 400th anniversary for Galileo's initial publication of his astronomical research, a lot of attention is being given to Galileo. So thought I'd work on the Astronomical League's Galileo observing club by getting one of the Galileo telescopes that are being marketed. I figure it will be interesting to people when I do observing nights for the neighborhood or for church and civic groups.
Once I buy that one, I'm sure all I will need is just "one more" telescope.