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


As a tinkerer in areas like woodworking, the old adage of "buy the right tool the first time" has always been my philosophy. This way of thinking seems to be somewhat at odds with my new interest in 2 channel Hi-Fi.  More specifically, what is the "right audio gear" the first time? I know many folks start somewhere and work their way up to higher end gear as their preferences/and budgets evolve.

My question are here:
If one has the means to jump into higher end gear, should they or should they start budget and work their way up?
If one does jump into higher end gear, would a newbie appreciate it versus those that work their way up?
Am I overthinking this?

This is an opportunity to openly state "what you should do .... comments"
128x128promero
agree w many of the sentiments expressed

as in most areas of passion/ significant hobbies, the journey is as important (if not moreso) as the ’end point’/current state of affairs

i always think about a parallel in the world of enjoying food... we are fortunate when able to experience variety, learn and try new things, experience new flavors, preparations... our horizons are broadened, our senses are stimulated and sharpened when we allow ourselves to experience what others have found to their liking
Many excellent and useful responses.  I bought my first system in the mid 70's so I have been doing this for a few years.  I have changed speakers five times since then.  Analog source has changed twice and digital 6 times.  My electronics (amp and pre amp) once from my first set up and multiple times with Herron Audio. 

Just my two cents is to nail down the speakers first.  This takes a lot of time and critical listening. You need to determine the flavor of the sound you enjoy as previously expressed.  I would then focus on the source and electronics next.  It can be one and done but you can probably guess that it usually doesn't happen this way depending on how long you plan on keeping the system. 

If you are fortunate to have a good dealer network near you, this is the best way find the perfect match for you.  If not, it will involve travel.  Shows are a good source to get an idea of what you may like but I would never make a purchase based on a show.  Good luck!    
Just like any other hobby, the amount of self education about what's available, how it works and what it costs is essential with the added caveat here of what does it sound like? 

If you have friends close by with good systems you can learn more much faster as you hear them. Systems in retail stores and at audio shows aren't usually an accurate guide to what that same gear will sound like at your house in your room but can give you a rough idea of price and direction.

Trust your ears. Read equipment reviews but realize they usually aren't as objective as you might think they are.

Finally, enjoy the journey. Music is the best.