I started the audiophile journey from the other side, as a HiFi guy reviewing home theater and stereo gear for several websites. I quickly progressed from the internet direct budget brands to some higher end speakers and amps, all the while trying to stack rank the products I heard and give a delta value (%) of how much better it was. I tracked this on an excel sheet, and slowly started to reach some conclusions about where the price/performance inflection point lay in this market.
I ended up purchasing a Paradigm Studio 100,CC690 setup and Wyred4Sound amps, a Marantz processor and a Seaton SubMersive subwoofer. Total cost - about 10k. It sounds as good as about 90% of the $25,000 setups from several manufacturers I have heard, yet delivers a lot of enjoyment. I have decided tentatively on my endgame speakers, and will one day be ordering them or their successor at a cost of about $10,000/pair. However the real lesson from all of this is simple:
Listen to the gear with your music, on your amp/source before making a decision. I did this with my recent headphone purchase and ended up going from 0->T90 and am extremely happy with the result. In home auditions are key for speakers, just like on-head auditions are key for cans.