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

I have a dealer that I trust which is a big help. I read reviews, watch videos and read forums like this, which helps to get an idea of the list of equipment to try to hear. Ultimately, nothing replaces hearing the component, preferably in your own room, but sometimes that is not possible. Doing research and getting advice can be very helpful in composing the list, but I think you have to be a little careful with how much that influences your decision. Trust your ears. People tend to recommend what they have chosen for themselves, quite naturally, as there is a lot of self affirmation in that. This is a very subjective hobby, however, and everyone has a different set of ears. Ultimately, it’s a matter of choosing well built components that fit your budget and sound the best to your ears, not someone else’s.

Online reviews; owner reviews; video reviews; decide, then purchase (almost always) used.

I think listening to the equipment first doesn't really work well as there are very few hi-end brick and mortar stores, and even if there is one near you the chances of them carrying what you want to listen to is not likely.

Buy, try, sell (or keep).

I look at the measurements on ASR then I send an email to the minion leader asking for his permission to buy the equipment.

No seriously, I read reviews and then audition the equipment, hopefully with the same or similar equipment that I own.

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.