What kills me about a lot of the technology we use today is that few people, at least in positions of power are brave enough to pause every now and then and say, "WTF are we doing?" So many technologies live on because of so-called "critical mass," big investments, marketplace skills, and other things that are about anything other than the technology itself. These of course are mostly practical reasons and important ones at that, but at some point it becomes impractical to continue to cling to the practical reasons. IMO, the ability to do something truly different to make an advancement is often what separates innovators and intelligent people from the rest. When someone does try to act, the market essentially crushes them accordingly, making most efforts null and void, and dulling the senses and hope of everyone else watching, warning them not to try anything themselves.
x86 CPUs, web browsers, popular operating systems, and so on are all examples of this problem. At some point I really wish we could do something different, practical reasons be damned. It's sad that as many cool, "new" things we have, some of the core, basic ideas and goals are implemented so poorly and we are effectively stuck with them. This is one reason I hate that almost all software and hardware projects are so rushed, and that standards bodies are the opposite, but with only the bad things carried over. The cost of our bad decisions often weighs for much longer than anyone could imagine, just ask anyone who has designed a programming language or something major in software ecosystems.
As much as I enjoy all the new, shiny stuff, it makes me sad thinking about BBSs and old protocols Gopher that represented the old guard, alternate routes, and the fact that we really haven't come that far. Overall things of course are a lot better, but in many ways I often feel like we're treating the symptoms and not the cause or just going around in circles.
I could go on, but the rant would be novel length.