I have my feet firmly planted on both sides of this fence, but my heart is grounded in the music. Some of my equipment is extremely expensive (at least for me), while other elements are definitely bargain bin selections. This goes for cables too.
Regarding speakers: I seem to always be seeking speakers that sound better than what I own. While several different ones sound great, none have motivated me to make a change. For awhile I was certain Sonus Faber, Magico, B&W (have owned three sets in my 2nd system and only have the center channel remaining), Vandersteen (had one pair in the 2nd system and now gone), the Yamaha NS5000 mentioned above, and many more. My Acoustat 1+1, that I purchased for $350 over thirty years ago (I am the third owner), that were refreshed twice over the years pushing the total investment to near $500 (not a typo) are my reference speakers (supported by an active SPL Crossover and a pair of Rythmik F12SE subs). The only speakers that I would replace the Acoustat pair with are a few different TAD models. Of course, the prices are astronomical and I cannot justify the cost. My Audiogon name reflects my approach to buying almost everything, but especially audio. Thrifty Audio reflects my goal of getting the best possible for a reasonable amount.
Enjoy what you have and only upgrade if it truly makes sense to you. Being an Audiophile is more a state of mind and absolutely nothing about how much something costs.

