no they did not really question it at the time.
At the time there was not any plug like it that could perform those function universally. You had printer cables (bulky as hell) tons of com ports device that yessed used large bulky plugs.
Thunderbolt really does not bring much new to the picture. It is massive over kill for most devices that could use it. So much over kill that it is not worth the cost to build devices for it.
Thunderbolt is looking to be like firewire and we all saw how firewire worked out.
Everyone was deeply suspicious of a cheap and simple USB port replacing all their legacy PS2's and DB9's and DB25's and bulky Centronics cables. Oh, wait, never mind. Everyone was happy to have access to a fast hot-swap port that worked with nearly everything and didn't require $50 cables or only connect with a handful of thousand dollar devices. The problem with FireWire wasn't that it was developed by Apple. FireWire was technically superior to USB by all accounts and found a strong following in professional markets. The problem with FireWire was that few commodity manufacturers were willing to use it and it remained too expensive to become a universal port. If it had been developed by Intel that wouldn't have changed anything.
Clearly you two are suffering from nostalgia-vision. I worked retail when the iMac and USB on Windows hit the scene, and it was a royal pain for customers early on. The plethora of adapter cables to let your old printer run off a USB port, or to run a USB printer off a parallel port. Mouse and keyboard conversion dongles. They didn't all work with all device/computer combinations, either, so good luck finding the right one.
Back then a base-line USB keyboard ran $35+, and a basic USB mouse was $45+. Those fancy new USB printers? They didn't come with a USB cable for some unfathomable reason, so you had to buy one along with it, typically $25 or so for a 6' cable. Need something longer? Good luck, and pull out the credit card.
USB *got* cheap and ubiquitous, it certainly didn't start out that way, and on the Windows side it certainly didn't start out problem-free either.