Mine started around 1996, when after 20 years of owning diff. audio gear, I bought my 1st "high end" speakers, & paid $2500 for a slightly used pair of B&W M802's. This was huge for me. However the rest of my gear was old NAD mid-fi components, & I knew I'd have to upgrade around the speakers.
I started by relying on Boston area dealers, who were mainly either rude, or clueless. (The one on Comm. Ave., wasn't bad, but didn't really help me much). The one in Natick, the salesman kept trying to convince me that large floor standing B&W's are "very efficient, & only need 30w of power (???). So I bought a 70w tube amp, guess how that worked out w/B&W M802's? The dealer in Waltham MA was the only really rude one; it's one of those really snooty audio "salons" that cater to the Rich, & you apparently are supposed to spread around $1000 bills every time you go in there. Oh, & a dealer in Nashua NH that tried to sell me $10,000 cables for my $2500 speakers (??!). The "pomposity" of some of these audio salesmen was unbelievable.
So I started buying everything used, on A'gon. I had 3 systems at the time, so anything that didn't work w/my 802's, I'd put in one of my smaller systems. Fast forward 14 years, I've been thru at least 5 of everything": pwr amps, preamps, spkrs, cables, etc. Had a lot of fun with the various permutations of systems. And finally ended up with 2 systems that I love, & mostly don't even want to change.
The learning curve at the beginning can be brutal tho....