In my experience, it tends to run along brand recognition lines more than anything. This is why Bose has good resale value. (on eBay; not on AudiogoN).
My speakers have relatively poor resell value because most people have never heard of them. I still would not have bought anything else. I like how they sound, and that is all that matters.
In many cases the more expensive an item is, the worse the resell value is regardless of quality, because the market demand at the ultra high end is pretty small. Also, people with unlimited cash to burn will most likely want new stuff.
My speakers have relatively poor resell value because most people have never heard of them. I still would not have bought anything else. I like how they sound, and that is all that matters.
In many cases the more expensive an item is, the worse the resell value is regardless of quality, because the market demand at the ultra high end is pretty small. Also, people with unlimited cash to burn will most likely want new stuff.