Having images piped directly to your PC and being able to control the telescope from inside is very cool and a must in my book (who wants to sit outdoors all night long in the cold, lol?). Ditto CCD. Amazingly, not so long ago, neither of these was possible. And the big scopes out there nowadays would astonish amateurs of 20 or 30 years ago. Just wish I didn't live so close to the city.
Maybe I'll start out with one of those 10" Dobs from Orion for $600. Just slew and look, easy peasy (but cold and uncomfortable). :-)
I am currently in the process of building a 8' diameter domed observatory to house it in, as the set up time can take over an hour, and then tear down time etc.