One thing to be aware of is that buying and selling may not work very well because you may never have a complete system that truly synergizes together all at one time. "Endless upgrading" as the topic discusses, may not be an upgrade at all but a bunch of sideways moves. That is why when I bought my most recent system I bought from a dealer that had not only the ability to match gear well, but was more than happy to work with me until we found what made me not only feel, but know, what worked well together and made the sound I wanted; note in particular it was about the sound I wanted because we don't all want the same sound. I've spent the last five or six years going to shows and dealers and I knew when I heard the speakers that I bought, if there was any way I could afford them, I'd bring them home. I brought them home with electronics including a server source that just sing together. I do realize that not everybody has local dealers they can visit and so not everyone can take this route to design a system. But if you don't have local dealers, going to a show can get you pretty close or at least push you in the right direction. Forums like this can help too, but in the end it is about what YOU think sounds good and so taking someone's word for granted may not get you what you want. The proof is always in the listening and of course if you can hear a system in your own listening room that is even better yet.
One more comment. I'm maybe five years away from retirement and thought I'd purchase my last system after I'd crossed that line and had even more time to research and go hear equipment. But then I heard the speaker that wouldn't let me stop thinking about it. I'm glad I decided to make it happen now as who knows, hearing could be worse in five years, I could get killed on the way to the gas station, whatever. We all have different goals; I've been a pretty frugal guy all my life and this was my one bid splash out. It brings me joy everyday, even if just using it in conjunction with my TV.