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

I used to do the standard thing of reading reviews and forum posts. I also bought and sold a lot of gear in the past 5 years and heard them in my space. That all worked well but these days when I need something I first check on the Schitt web site to see if they have what I need. I have sold off a few pieces that cost a lot more money than the Schitt item that replaced it.

For example, the 2 Yggi+ DACs, 2 Aegir amps (headphones), Mjolnir v3 preamp (headphones). That is over $20k in expensive gear replaced by under $5k in gear. 

I read as many reviews from as many different places as I can, focusing on objective measurements first followed by a listeners impressions. Where I live there are no serious audio stores within 3 hours from me, so auditioning is not really an option. That means everything is being auditioned in my home and I am nearly always buying new so I avoid the unforeseen problems that can occur with buying used. Warranties are a good thing if the company is good, often not worth the paper they are written on. I have read so many horror stories about poor customer service from companies like Denton, Yamaha, Marantz that I have written off most of them as unacceptable risks. That said, because sometime over the next year or two I will be replacing almost everything that was in my home with new, I am reading as much as I can and also rethinking how to do things so I end up in a better place than I was before the fire. Sometimes less is more and I am likely going to test that idea and see how it suits me.

@oberoniaomnia

RE: "Listening is a pipe dream".

Upscale Audio is one CA dealer that offers a return policy.

There are plenty of others online.

Audio gear purchasing need not, by definition, be a "shot in the dark" -- it’s your choice, ultimately.

For me, buying without a home demo does happen, but it's extremely rare.

Not saying what you ought or ought not do, just pointing out there are options.

I have auditioned every piece of equipment in my system in my home and every component came from a dealer in another states with the exception of my speakers. It can be done. Naysayers are foul o the crap and did not even try to do the work. Home auditions will save a tone of money and earache. 

@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.