My upgrade paths typically led to equipment that was noticeably better with the "I'm there" sound quality I'm trying to get to. It typically meant that the piece I'm interested in is one or two levels up from what I currently owned, but not the "top of the line" currently offered piece from that manufacturer.
This is good for me because in this "hobby" there are many that are in the amp of the month club and they have to have the newest, latest and greatest piece offered and trade in or sell their previous piece when they get the latest and greatest newest piece.
That opens up opportunities for people like me to finally get that piece that I wanted. For example, the latest piece I purchased a few years ago was an Audio Research REF 6 pre-amp. I wanted on because I did an A/B comparison between that and my previous REF 3 (re-tubed) pre-amp. It brought me closer to "I'm there". But, I couldn't afford the REF 6 new. But, many bought the REF 10 and a few years go by and the REF 6 came available used for a decent price. Still more that I was willing to pay, so I waited. One of my favorite dealers informed me of the Audio Research trade in-trade up program a few years ago.
Long story short, I upgraded to a REF 5SE first. Used of course. for a decent used price. Better than my REF 3. Sold my REF 3. Then the trade-in/trade-up program came and I received 75% of MSR for the REF5SE. Do you believe that? I got more for the REF5SE than what I actually paid for it, applied to the REF 6.
I really want a REF 10, I've heard it several times (even in my system) and wow! What a pre-amp. But, even used, it is not at a point where I can "justify" (love that word in this hobby) purchasing it .
But, eventually, when Audio Research comes out with a new pre-amp that is much better than the REF 10, people will sell their REF 10s and go for the newer pre-amp and open up the opportunity for me to get the REF 10.
Used is always good if the price and condition is right. Same for cars. Why buy a brand new car with ridiculous dealer markups and immediate depreciation when you can purchase a used excellent condition low mileage car for much less, with full warranty, etc.
anyway, my thoughts.
enjoy