Opinions on the current market

The simple answer is to "get out and listen" and if possible "try before you buy".

That’s the only way if you want to increase the chance of getting it right the first time.

/ Marcus, www.perfect-sense.se (high-end audio consultant)

I agree to a point. It’s impossible to hear everything first, and doubly so to hear everything, in my system, before buying. I’m going to have to take a risk and theoretically, multiple risks. The first piece I buy may improve my SQ, but still not be the ‘right’ answer. I’m looking hard at some older, higher line pieces in the $2K range. Hoping the depreciation is mostly done, and I could recover most of the dollars if needed. 

Spend some time investigating the used market to determine which preamps have stable values and which do not.

Audible Illusions and Audio Research are 2 brands that have great reputations, and hold value over time.

Vintage Marantz 7c or McIntosh C20/C22 also hold value.

If you were to audition one preamp from each of the above, you will likely hear different results from each when added to your system, hopefully allowing you to choose what sounds best to you.  Then the others can be resold for what you paid (or maybe a little more....).    

The big difference of late is there is no place to go to listen to hear before buying. No shops or shows. Not sure what effect of any that has on the market overall but has to be bad for anyone selling new stuff.

@mapman I heard an interview with Jeff Joseph on Stereophile's Youtube channel and he said that while he is selling things, with something of a return policy, business is undoubtedly slower. I was even entertaining some Ohm/Walsh speakers, which sound like a good deal -- free shipping. But only free shipping TO me, not free shipping back to them. So, not cheap to try. PS Audio pays the shipping each way, so that's a nice way to really try things without risk.

All that said, it really doesn't take long to rule something out in a store. If I listen to 5 sets of speakers in an hour, I at least narrow it down. The idea of paying and having things shipped to me seems like a good approach -- if I have already narrowed it down, first. But, as you point out, that initial listening experience is SO key.