Well, first, depending on the type of music a smaller system can sound pretty good but not on everything. Secondly, friends ask me how I can listen to a $20 radio at work when I have such a nice system at home. I like music; it is that simple. However, when I really want to listen to something that can give me chill bumps, it is not going to be on my little radio.
My advice is that maybe you have hit a wall where you additional investment just isn't bring you any additional "joy" (for lack of a better word). Maybe it is time to quit tweeking or upgrading and just enjoy what you have while you decide on a plan. Downsizing may be an option or maybe finding a new type of music that really turns you on will help. For example, I was talking to a friend who had asked me if I had ever heard of a kind of new age flamingo by Jesse Cook. I borrowed a disk and for the next few months was really energized by this incredible music.
Don't worry. I am sure we all are there at some point. Something will happen to re-energize you!