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

Am I overthinking this?

Absolutely not!!! You’re asking very rational and intelligent questions. Having been a 2-channel audiophile for about 40 years (ugh) and looking back, I would’ve made HUGE (and very costly) mistakes if I just jumped in and threw big bucks down on what I thought I liked at that point. Look at it like wine — would you start with a $10k bottle or start lower and let your tastes/knowledge base grow and evolve before going big?

The good news is you can get some really excellent gear and build an extremely satisfying and rewarding system for not all that much these days, and even more so if you’re willing to buy used gear. First, and MOST importantly, you need to go and listen to various systems to start to identify what sound characteristics are most important to YOU personally (using your own music as well as some well-recorded demo material) and then you’ll be in a much better position to take a good first stab at putting together a system that’ll really make you happy. Then, as you listen to it for a while and hear more gear at shows or wherever, start to identify what improvements you’d like and upgrade one piece at a time until you’re completely happy (good luck with that part). Oh yeah, and READ as much as you can to learn more about both the technical aspects of audio and other products out there so you’re in a better position to make good choices later.

As a VERY basic guideline, starting with a $10k budget you could buy $3k speakers, $4k integrated amp, $2k source, and $1k for cables/misc and you could have a REALLY nice near-full-range starting system. Unless you feel highly confident in your ability to choose gear at that point I’d hesitate to spend much more than that (remember the wine example). Anyway, looking back and if I was to start over even with a big budget this is what I’d do FWIW. Hope this helps a bit, and WELCOME the the wonderful, awful world of higher-end audio!

If you have the means to pay full retail, then visit as many dealers as you can, to find one that is reputable and that you trust. Then make decisions based on what you hear from there.

There’s only one acceptable system here on Audiogon...something, something, swarm, springs, and fuses. Repeat until death.

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?

Not at all. I think you will find it difficult if not impossible to master anything without a lot of deep thinking. When you have done that and mastered this to the extent that I have the hardest part of knowing what advice to give is knowing what the other person wants. Therefore I say the First Rule of Audio Club is Know Thyself.

This is what it pays to think about: What exactly do you want? The better you understand your own desires and goals the easier it comes and the more likely you are to succeed. Otherwise it is real easy to get swept along in what everyone else wants. Look around. Click on their names. Look at their systems. Read what listeners say. Is that what you want? Serious question.

The way I see it there are two main paths a guy can take: One and Done, and Work in Progress. To do One and Done you take whatever you feel like spending and budget it out into all the things you need- speakers, amp, source, wire, accessories. KISS- equal amounts for each. The budget is really just a way of forcing you to recognize every component plays a part in the whole, and keeps you from blowing your wad on sexy speakers and amps leaving you screwed with lamp cord and freebie rubber power cords.

Work in Progress can start out like that. But with this one slow and steady wins the race. With WiP it is okay to spend half your budget or more on speakers. Or turntable. Whatever. You can do this when you find something you really love and know you will continue to enjoy for many years- during which time your whole system grows up around it. Until one day years from now that piece that was once your shining star is now just barely holding its own. By now you have had it five, ten, fifteen years and your whole system is now comprised of similar shining stars. This is exactly what I have been doing, going on some 50 years now.

Your job right now is to figure out which one you are, how much patience do you have, and perseverance. Because once you figure this out the rest pretty much falls into place.

Good Question OP.

What room will it reside in and for how long? That matters. If you are in a home and your listening room will not be changing for the next 15 years, then your build will not need to be flexible. For instance if you are in a 12x16 space La Scala may not be the right choice. Silly example, but the size and space you are working with will matter. I’m a builder by profession and yes, buying the right tool first has always been a good idea. Same w/Audio. Save and buy quality. Buy Demo when you can. Determine if you like Tubes, SS or both. Determine if you like Conventional vs Planar or Dipole Speakers. Take your time, wait and save, buy slightly above your affordability level and most important of all, hide this information from the wife.

good questions indeed, as per @soix

question is what budget level for a system (and don’t forget the quality of the room/listening environment)

under a grand for a system is quite challenging (despite what talking heads on youtube say)
2-3 towards 5 grand starts opening door to a very nice sounding system, if using a single source
10 grand and up accesses some excellence, so long as the room is not too large

i am talking smart buys of used gear here