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

I pick my gear only after I have consumed a lot of adult beverages, it's my cardinal rule.  The darnedest gear shows up at my door step sometime later and I just shake my head... I did it again.  Great gear comes and great gear goes, I am just along for the ride and it is whole lot of fun along the way.  You could say that I really don't overthink my gear acquisitions. 

I like visiting dealers.  I appreciate hearing things in person.  The last few transactions were with local dealers.   DAC,  CD Transport, Cartridge, and  Pnono pre.  I got really good deals on all.  

I try to buy something for the long haul, it doesn't always work out but I'm happy with the items mentioned with no desire to upgrade anytime soon.   I think it's  mostly because I heard them in person, then in my home with option to return.    

I read reviews, but more to learn about the feature set , capabilities,  etc.   I let my ears decide.  

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.