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I don't think the guitar prices have anything to do with baby boomers - whatever that means, I'm 48 and that means I'm too young to really place these guitars in that high esteem because of a hero, if that was the case I should be buying early 80's Kramers and Charvels.
There are two distinct markets, the investors who want the minty examples - these are purely looking at historic growth, and in an age of miniscule interest rates and the cultural memory of the credit crunch investors are much happier to invest in the physical than the virtual - not surprisingly, that's not restricted to guitars - you see it in watches, cars, furniture etc.
Then you have the more player grade stuff, and largely I think those prices are set by the manufacturers - take Fender for example, a new team build Custom Shop Strat will be what £2500-3000? And a Masterbuilt £4500-5000? don't shoot me over these prices they're ballpark.
Based on those, it makes complete sense to say - ok I can get a Masterbuilt 'copy' of an old strat, or I can get a refin'd original for 'only' a grand or two more. So that sets a base level for the refin Strat market, I don't believe you'll ever get a situation where a modern reproduction (as good as it maybe) will be worth more than what it's copying.
From this baseline, the higher levels of player grade will progress, ok well it's not a refin but it's been played hard - that's worth a bit on top of that etc.etc.
Similarly with Gibson, where you have Collectors Choice guitars retailing at £7k plus - a conversion of a 50's Les Paul, or a nice example of a late 60s has to be worth at least the same and likely more. Why? Same analogy.
And this is not taking any account of supply and demand, there are less old ones around - I've recently got a wonderful (good grief the neck is good!) 64 SG, I could only find two other ones for sale in Europe, with only one other for sale in the UK.
It seems to me many people are wanting prices to fall, I don't think this is helped by places like Reverb which has a bizarre combination of high asking prices and then very low price guides. The price guides are fundamentally flawed in my opinion, firstly I've bought two guitars I first saw on Reverb, but for perfectly legitimate reasons I bought off the site, so those statistics are not counted and also the condition is set by the seller - how can a refinished junior with a heel break, replacement tuners etc be described as excellent? Yet you will see that, and the price will look artificially low.
There will of course be ebbs and flows in the market due to economics, fashion etc. but given the choice between a guitar made at the original factory, with the 'correct' woods for the model, which has been played and maintained over the years vs a modern copy where conservation (which I fully support) has dictated what wood can be used and the ageing has been simulated I know what I'd take.
Modern guitars, can and are great - I love my Feline superstrat and I fully expect my next guitar purchase to be a Strandberg 7 string. Fender, Gibson and any number of other manufacturers are making great guitars.
But there are many facets as to why some people choose a mixture of old and new, or just old.
Also, whilst we're talking a lot of money - look at any other hobby, as others have said - how much money do people spend on owning and running cars? 3 years ago I stopped car ownership completely, and I can't believe how much money I've saved. Let alone how much money 1000s of people spend on mountain bikes, golf clubs or an old hobby of mine - clay pigeon shooting, you will regularly see people shooting (not that well!) with a £5-15k gun, £500+ sun glasses etc. I would regularly spend £50+ a week on shells and clays and I wasn't even considered serious.
John Lewis has Sony TVs for £3000, these are selling regularly and will be worth 10% of that in 5 years time, yet I sit next to any number of people who have 'invested' in something like that, and a Xbox and numerous games etc.
We live in an age of disposable income, and people looking for things to enjoy - I think vintage guitars fall squarely into that.
Yes some dealers try and hype the market, but there are some wonderful guitars around for less than the price of a new telly
Ref prices - I've been buying and selling guitars for over 40 years now - And the discussion regarding rising vintage prices has been going on most of the last 4 decades - I'm not a pure vintage specialist, certainly compared to other dealers/sellers, but I follow the market and have sold many examples during my time at the crease - I own a few nice examples but I'm not a purist vintage buyer/player compared to others
I recall in 1978 buying my first 62 Strat for £375 - refin nat body, but otherwise every nut, bolt, screw etc was 100% original so a good example - At the same time I could have purchased an all original example for £500 but it did not play as well IMO
Therefore in the last 40 years, that £500 original version has now risen to around £12,000/15,000 - So pushing around 30 times the 1978 value - Could I have made more investing £500 in some other avenue ? - maybe, maybe not, but would it have given as much pleasure, as well as an investment , as the Strat
Are they worth these prices ? - Will they fall ? - Will they go up further ? - As I mentioned above, these discussions have been going on for 40 years - Prices will/can only fall significantly when there is less/no demand and who can be sure if/when this will happen - It doesn't mean we/you have to be part of it, no matter if we like it, or indeed can afford it
Bottom line is each to their own - There is some magic in many old vintage guitars, but not all - There is some character in many old guitars, be it cool, odd ball or weird models (@harry7 will vouch for this ) - many 'player grade' vintage models that have been worked on/customised etc play very well and as @peteri states above, examples can be purchased for a similar price to a Custom Shop Vintage Replica