Like others said, Schwinns were always more expensive than Sears,Western Auto and other bikes in the 50's 60's. It was a real treat for a kid to get a Schwinn-you didn't have to be rich, but they were expensive.

In 1968-69 the more affluent kids in college had Varsities-which were about $150 I think.Schwinn had some sort of agreement with its dealers-THEY ABSOLUTELY WEREN'T ALLOWED TO DISCOUNT-THEY HAD TO SELL FOR MSRP.
In 1970 I spent lots of time at a local bike shop in Baton Rouge. They showed me a $300 "chrome framed' bike with tubular tires. Like a fool I thought it was too expensive.Heck it was only 2x a Varsity, and it was literally about 1/2 the weight-maybe 23 lbs or so vs 40 lbs. I finally bought a POS KOLKOFF (a cheapo W est German bike) which dropped me one day when a chain stay brake at the BB(yes,I got it welded back for $5). 3 years later-1973-I paid $330 for a Bottechia Pro -double butted tubes Campy record crank, derailleurs, headset, but Universal ??63, 53 (I can't remember center pull brakes-didn't work very well).
Guess I should have bought that overpriced "Chrome frame Schwinn"-might have been full Campy-certainly lots of Campagnolo, but I had no idea who Campagnolo was then.

Around here there are some flippers getting $200 for Varsities etc. The 80's Asian bikes with Chrome Moly frames are better bikes,and usually cheaper. Yes, there are plenty of "collectible" Schwinns being CL here- but the prices are high.
I don't think the prices will ever be high.The buyers are baby boomers and the generation after them. The lure of hauling a 40 lbs bike up stairs fades after a few rides-especially for 40-50 -60 yo riders.

Just haul one up the stairs a few times- it will tell you all you need to know about future prices. Try to hang it on the upper rung of your bike rack-NO FUN, RIGHT!!
A 10-18 yo kid didn't care what a bike weighed-the rest of us do.It had little to do with speed or climbing-except climbing stairs with that hunk of steel..

Charlie