Light polution is a pretty big issue as urban areas grow. Naked-eye observing is almost impossible from our yard. If I can see a magnitute 2 star, I feel pretty lucky. The new CCD/software packages seems to address this problem. Unlike the old days, telescopes can now be completely interfaced with home computes to the extent that one can sit at the kitchen table and observe with complete control and comfort. I used to like freezing my ass off just to look at the perfect sky, but now I'm way too old.
I would love to have private observatory. Two issues would concern me: convenience and security. I have a hard enough time just walking downstairs and listening to my system. Also, theft and vandalism would always be a real possibility.....C