We are the same age and we have seen the same progression of technology. I would argue that some of it is analagous to amateur radio. BBSes and some aspects of the Internet are very much in the spirit of ham radio. These are technologies that people used for communications and where people experimented as amateurs rather than as professionals. Just as radio amateurs created their own networks of repeaters, people setup networks of BBSes (e.g. relaying between BBSes or wiring LANs).
I think that amateur radio faultered when it became more like online service providers or the modern web: people continued to use what was there, but it stagnated since few were experimenting and few were interested in creating infrastructure.
I also see that attitude leaking into our online world. Consider something like Gemini. Some people experiment with it (as either developers or for communicating with others), which is very much in the spirit of ham radio. Yet there are also numerous naysayers, those who see their fancy new rigs (or web browsers) as being the only true measure of progress even though they can only partake in that world as the modern version of a ragchewer.