Buying the right tool (aka gear) the first time...

I think your thinking about it the right way.

8 years ago I separated my home theatre from my listening room and over the past 2 years I've effectively replaced my system.

If you live near a big city with a reputable dealer I'd suggest you sit and listen to a bunch of stuff with them to have you understand a bit of the options.  Then listen to any system you can - even from the dealers with less than stellar reputations to gain some perspective.  (Even a bad perspective can be enlightening).

One of the best things I did during my upgrade path was talk with my dealer and let him know my path because I was able to get several used items demo and a customer who tried something different and didn't like it.  It was a win/win because the dealer got to happy customers.

I've found over many years, if you don't do, you don't learn. It took me fifty  years to get the system I have now. If you don't have deep pockets (such as myself) it's a bit harder to finally end up with a system you really love. It can be done, though.

Having the right room is just as important as having good equipment. When you have both, you can be in  heaven.

It helps if you have knowledgeable friends to help you access good equipment and listening enviroments. Take your time, and enjoy the process, it's a long road.

Best of luck, and regards,
Dan

Excellent responses on this thread. Keep in mind you can spend a lot of money on a piece of stereo equipment and not really care for its sound. You can also be floored by something that has no right sounding as good as it does for so little. Generally yes, money is going to buy you better quality but not necessarily the sound you like. A lot of us on here love music and love the gear. We just like trying different stuff to see what floats our boats. Islandmandan sort of nailed it for me. Good luck to you and I hope you enjoy the process. Best advice, don’t get as neurotic about this as a lot of us loons.

Are you the kind of person that constantly second guesses yourself? Have you already “been there, done that” enough so you can categorically state preferences without doubt? Do you have a budget in mind or a performance goal? Are you in a hurry?

if you’re starting from scratch it might be worthwhile to buy budget used gear of different types to compare, especially speakers, so you have firsthand experience rather than just blindly following a bunch of yahoos on the internet. This will clue you into your personal preferences and help with setup. Don’t skimp on room treatments though. Budget those for where you want to end up. Every system can benefit from a better room. (I’ve often thought that at some budget level designing and building a dedicated room is more economical than fighting a poor one.)

Once you think you’ve done your research start introducing endgame components into your starter system. It’s probably best to start with speakers and work backwards: amp, pre (if needed), DAC, phono stage, sources. Get appropriate cables as needed. Don’t be afraid to change your mind along the way if priorities change. You may end up with more than one system or a bunch of great gear that you mix and match based on whim or mood. You may find as much entertainment from adjusting your system as you do from listening.

Alternately, ask for recommendations for a great local shop. Tell them your budget. Audition equipment. Trust their expertise. And be done with it. 

Buy whatever sounds good to you. Can you do that? Or do you want an assortment of characters to plan for you and set a budget?