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

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

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.