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mmccarthy
As someone who has just spent £5,500 on a seiko, albeit a limited edition Grand Seiko, I'll give answering your question a shot...
I own a few 'expensive' watches and a plenty of cheap ones too.
For me, I see value in the engineering, finishing and attention to detail as well as the historical or 'heritage' elements too. More importantly for me though is probably the memories associated with each watch...
My Rolex Explorer was bought to wear on my wedding day. An Omega Seamaster gold cap I have was purchased with a small amount of money left to me by my grandmother. My Nomos Metro was bought to celebrate a promotion at work, etc etc.
Going back to engineering, I own normal seiko watches which cost me between £50 and £150 and the difference in quality between that and the Grand Seiko or Rolex is vast. Is it worth a 10x, 20x or even 50x price difference? I guess that's up to the individual. Personally, I've never felt disappointed with any watch I've bought in those sorts of price range.