I have to disagree with you on the "keeping up with the pinhead" comment.
Collectable items are generally considered to be an inflation hedge, a way to protect wealth from inflation when the stock market is doing poorly.
I mean true established collectable stuff like stamps or coins or antiques.
Not stuff that's specifically made to be collected like Disney figurines or fads like beanie babies.
If you sink money into a decent collectable like firearms, coins, stamps, generally you will at least get your money back plus inflation when you sell.
Sometimes a collector market will get hot and turn into a very nice investment.
Like for example, 60's muscle cars were selling in the $10,000 range until they suddenly became red hot in the early 1990s and now some of them are worth $100k+.
Pinball machines are collectable, they are "Americana" like vintage jukeboxes.
I think there's always going to be a collector market for 80s and 90s pinballs.
On a side note, to be fair, even though Rolexes (in my opinion) are grossly overpriced, they hold their value very well. A guy with a rolex collection is probably going to make out just fine.