OP,
It's the never ending journey isn't it, the question is where does someone decide to get off of the merry go round and be happy? I'm not near there yet.
I love my current set up as it is very enjoyable and musical, but I know that there is so much better sound out there. With my new Clayton Shaw Caladan speakers (coming in February?), I'm at about $19,000 and I still consider my system the lower end of mid fi. I'm buying a new tube preamp in the next few weeks, a new streamer late spring, and I've got more than a dozen DIY cables to make over the next few months. After that I'll enjoy it for a while, let the cable configuration settle out and regroup.....but I'm in a very itchy upgrade swirl right now.