i was just having this conversation today with my roommate. i was talking about rare old bikes, and why schwinn's still command so much money, compared to almost everything else from the same era.
here's my thoughts:
from a "picker" standpoint, people who aren't going to ride the bike, might display it, but most probably will just try to turn it around and make a buck, you can't beat a schwinn. it's well known, even to people who know nothing about bikes. it's got the heavy nostalgia factor, as they were the majority of the market when we were all growing up.
i think this is what keeps the prices of a schwinn so high. there really isn't anything special about it, and as scott pointed out, they made that horribly awful (my opinion) cantelever frame design for longer than most of us have been alive. and it's still copied today. not because it's a great design, but because it's so recognizable, and doesn't take any design skills on the part of the 20 chinese manufacturers who knock them out today.
the schwinn straight bars were very plain, as far as design's go, and schwinn liked to dress them up with fender bombs and other novelty items.
but the main factor i see is that they were easily obtainable throughout the years. they were such a big player in the industry, with their own authorized dealers and stores, anyone could go down and buy their kid a schwinn for christmas without giving it any thought. "i'll take the blue one for timmy and the red one for sally..."
i don't understand how such a common bike can still command such outrageous prices though. pre-war schwinns are an almost daily occurence in the OC and LA craigslistings. the comparison to chevy and ford doesn't hold water in that sense, because if you're looking for (most) used replacement parts for your 57 chevy, you can pick them up for next to nothing and not end up sacrificing your mortgage for a bolt stamped AS.
they were well-made bikes in the "olden days," but after the 70's boom, produced lackluster bmx bikes and crappy ten speeds. if you showed up at the dirt track with your scrambler 36/36 that weighed 50lbs, you were gonna get laughed at. at least until the guy with the Huffy and his buddy with the Team Murray showed up (sad how all 3 companies "sold out" for the department store money.)
but back to classic bikes.
i've never been a hardcore collector, and i'm definitely not the most knowledgeable, but i've had cool older bikes since my teens, mostly 'cause you need a cool beach cruiser if you live in souther california, and schwinn's weren't on my list.
i've always went for the oddball bikes to set myself apart from everyone else.
currently, i think the pre-war colson's had it all. the loop-tail rear end is beautiful, unique, and the snap tanks, the gills, the bullnose, the giant chainguards, and everything else compliment each other perfectly.
and dude, a "steer from the rear" tandem? now you can look at your girlfriend's, uh, assets, and still be the one steering the bike.
the shelby's are another awesome bike, as are the Huffman's and the elgin's.
another thing i consider, is take off all the fancy tanks, racks, chainguards, and all the bells and whistles (as most of these bikes are found anyway) and see what you have. a shelby airflow frame is still beautiful, a colson still has the looptail, and a schwinn looks like every cheap beach cruiser ever made since the 70's, and you can't tell the difference between it and a walmart huffy until you're 2 feet away. and if you tell the average tourist on the boardwalk, "hey,but it was made 70 years ago!" they'd probably tell you it's about time to buy another one. they're on sale for 79.99 at walmart...