I've found that I can be happy with what I call mid priced gear so I don't feel the need to buy the big ticket items.
My main gigging amp is a George Benson Hot Rod Deluxe that goes for $1,100 but I picked up two of them for $600 each used in mint condition. They're great for Jazz and I have no need to buy anything more expensive to gig with. For a while I was gigging with My Sig:X and then a Mesa TC-50 both of which have their own distinct character but neither of which made me want to get rid of the Benson HRDs.
I got my 2001 ES-335 used in mint condition back in 2004 for $1,800 and it's one of the best guitars I've ever played. 21 year old Memphis Dot Reissue and it just sings.
No need to get a Collings or something comparable.
Same with my Fender American Deluxe Stratocaster HSS QMT purchased used in mint condition for $1,000. That guitar is so good I have no desire to buy anything else, including something a from a small builder that costs over $3K.
I think once you get out of the best of the $1K range you can be talking about diminishing returns regarding the cost/benefit ratio. It doesn't matter what the year or who the builder was, each guitar and each amp stands on its own. If it's a great example of that build then it stands on its own no matter what the cost.
That doesn't mean the expensive stuff isn't great. Much of it is, and in addition to playability there's the pride of ownership factor. But I've been as happy with my $1K and below stuff as I am with my +$2K gear, both guitars and amps.