A friend and I were talking last night and made the comparison between conspicuous consumption in the guitar market and how it is similar to the audiophile used gear market. There was some truth hidden in all our nonsense. It may also reflect your feelings on why you may feel you're hemorrhaging your hard-earned dollars.
I was a guitar nerd long before I was an audiophile. I had memorized all the specs of my favorite Martins and felt fortunate to save up the $750 or so to buy my first Martin, which I still own today. When I was a freshman in College, that was hard-earned money, and the only other thing I spent my summer roofing job cash on was my first stereo, a Harman Kardon preamp/amp and a pair of B&W bookshelf speakers. Both the guitar and the stereo lasted me until about ten years ago, when my disposable income blossomed. My thirst for better equipment became hard to slake.
I specifically remember the moment when I realized Martin was, for me, the Holy Grail. I played an Eric Clapton model 000-28 and realized "Oh, that's what everyone's making a fuss about." That's a theme with both audiophilia and guitars. When one becomes aurally sophisticated enough to appreciate smaller differences, the financial penalty becomes easier to accept. While I technically suck as a guitarist, I can claim that years of ear training has enabled me to sort the wheat from the chaff.
So, began my inevitable slide towards more and more expensive equipment, and the resultant rate of diminishing sonic returns. There was a point, however, when I jumped from a decent modern entry-level Martin into a different atmosphere, a vintage Martin. This was rarefied air in which people spoke with respect about "THE '37 D-28" or "THE '30 OM-28." Well, one could never reach that, could they? Turns out it's possible, if one has patience.
When I first started getting serious about my 2-channel setup, I donated my H/K and B&W speakers to my sister, who popped an aneurysm in ecstasy. I then had some salary cap space to get a great preamp and power amp from Vinnie Rossi and a pair of heirloom-quality floor-standing loudspeakers from Jeff Joseph. I can't imagine the system sounding any better. Also, those components are long-term investments with slow-to-change technology that should be satisfying many years after purchase.
Where I (and many of you) hemorrhage disposable income is with the digital components, DACS, streamers, etc. How does one protect against automatic obsolescence in which the streamer is, like a Porsche 911, instantly worth 20% less as soon as one drives it off the lot? I'm not sure I have an answer to this question, but I think it's evident that the logarithmic rate at which digital streaming and DAC technology is happening, we should all be prepared to trade digital components often. Those JA Perspectives? Not so much. I can't see them becoming obsolescent any time soon.
This is also similar to the vintage guitar market. Vintage acoustic guitars, at least over the past ten years or so, have been less sensitive to abrupt micro-swings in market value compared to their electric counterparts. Sure, some '58 Les Paul Sunbursts have commanded $250K US, but they are the super-flamed, or celebrity-connected examples. Most are more around $125K US. Vintage Fender Stratocasters and Telecasters have seen plenty volatility as well. Strats and Les Pauls suffer from more extreme market fluctuation during unstable economic times because they are influenced more by fad and fashion than vintage acoustics.
Just as vintage acoustic guitar, such as the OM-28, seem to consistently hold their value because they are stable technology that will not be overshadowed by more modern replacements, and one should respect these instruments. The same is true of classic legacy stereo components--a great Mark Levinson Preamp, or a pair of Wilson floor-standers.
I try to spend my money where I think I will get the best value proposition. I "invest" my serious audio dollars in classic, stable, time-tested technologies, while trying to keep up with digital gear without blowing my budget. This plan has worked well for me, and it may very well also be your plan...