Are there any road related things from the past that you think are cool now, but you would have hated them if you had lived back then. Missouri's shieldless route markers are a good example. Since they are from the past they are almost automatically cool but if I had lived back then and come across these signs I would have been very disappointed and I would have hated them. The first time I saw one I would say "stupid contractor" but if I saw a bunch of them I would get a sick feeling in my stomach. What objects, locations, vehicles, policies or other manifestations have become cool over the years but that you wouldn't have liked if you had lived when they were common.
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Cutouts. They were still somewhat common in this area of Kentucky when I was a kid. I thought they were cheap-looking back then.
$1 per gallon gas. People really didn't want to see an extra digit added to the price, but now, if any can be found, it's extremely inexpensive.
Back in the old days you didn't advertise you played video games or had a computer unless you wanted to be labeled a "nerd" or "geek." Being someone or intelligence was far less valued just a couple decades ago.