How do you pick your gear? Tips and insights are welcome.

First, it takes a long time, say a year or two. YouTube reviews, assorted Bulletin Boards, on-line reviews, manufacturer inquiries. I am looking for reviewers who cut through nonsense. Eventually, it is a product that gets frequently recommended, fits my needs/wants. Typically, there is a lot of back on forth in my mind, and then suddenly there is clarity. That's when I order it. 

I bought a Holoaudio May DAC L2 based on goldenear's review, following his debunking of MQA. Contrast that with Hans B., heavy on the MQA bandwagon and going on about jitter (is that even audible?).

Bought PearlAcoustics Sibelius speakers based on assorted reviews and being intrigued by 1-way Voight tube design, plus solid wood construction as a wood worker. Plus the most wonderful interaction with Harley Lovegrove. Love those speakers.

Bought a Rega Naia package based on Harley's shoot-out, CheshireAudio, Sales rep. Was a bit against my original thinking (heavy vs. light), and in the end went for top of the line light. 

Listening to equipment is a pipe dream. Is not happening. At shows they do not have the equipment I am interested in, dealers can't set up true comparison systems. So it is a bit of a shot in the dark.

Recommendations by sales people generally is disappointing. They will only recommend what they sell (obviously), so you will never get the full picture. I bought a PrimaLuna 300 pre, but for power went with Pass XA25. The only dealer for PL is not selling Pass, so they will never suggest the combo. Was through Harley, London shop video, and a bit of California state bias (I live in CA, where Pass is at home), that I selected it. 

Looks are a minor component. E.g. Macs are out because they are the worst combination of ostentatious and ugly. One reason I selected the Pass XA25 is because it does not have meters.

@suartk Re Upscale, I tried to set up a demo with plenty of lead time for some TTs when I had something else going in LA. They flat out would/could not do it. So in-store demo is a pipe dream. It is not possible anymore if you have something specific in mind.

The question I had is "do TT plinths have different sounds?" So I asked them to set  up a couple of rigs with same cart, same PS, same amp, same speakers (all their choice) just different plinth-arm. They could/would not do that. Said they do not have the material for that. In theory, I would have loved to see whether I can hear ANY difference, regardless of room. So much for providing education to potential customers. How it sounds in my room vs. dealer is secondary to whether I can hear any difference in dealer show room. That's why I consider dealers rather useless.

I still don't know whether I can hear differences in plinths. People argue there are differences, but I do not have first hand experience with that, despite trying.

Side-by-side comparison with multiple $20-40K rigs with intention of returning a few, that is equally a non-starter. Doing it over longer time, one at a time, raises the issue of long term audio memory being infamously poor. So you would need all the gear at the same time. And that is where dealers might come in. But they fail me as the customer.
Re ordering something with some >>0 probability to return it, I would not call that a demo. And upscale coming to my house with a few rigs to set up and run through, that is also a non-starter. 
So I did my due diligence with assorted reviews and bought a Naia package. Unheard, but with decent expectation of success. I'm happy with the end result.

Same with several other purchases from upscale. Specific demos is just not happening. Sorry. That is my experience.