my response is that any examples more than 20 years old are not relevant to modern day.
This is not categorically true. Sure, there may be/are past failings that may be circumvented by modern technology, but you'd have to do an in-depth analysis to find out whether that's true of each and every one of them.
Sure, but to point that out immediately moves the discussion beyond the scope of a forum debate. I believe that if you did in-depth analysis of all the details, it could in the end be summarized as true in a broad sense. That is my unbacked assertion, and to back it, I'd need the details of most interest to analyze.
Sadly what you or him or I want out of society hardly matters. What matters is what most people want - and material comfort is pretty high on that list. If your ideology (I don't use that word with a negative connotation, by the way) does not account for that, it will never pick up. The Soviets had to learn that lesson, the aristocratic industrialists had to learn that lesson. There's no way to impose a societal order for any significant amount of time if it is not accepted by a broad majority.
Yeah, and this is an unfortunate character flaw of mine. I've come to very much understand that I don't connect well with most of humanity. I simply do not value the same experiences, and the society we have is really bad at offering the things I do value. The only luxury I really care for is a nice computer, which isn't a material comfort in the same sense as a big house, expensive car, etc, and I've never felt the need for those things.
The thing that's never made sense to me is that even granted people's interest in material luxuries, what's the point in accumulating them if the process of doing so allows very little time for actually enjoying them? Yeah, you've got a nice house full of nice stuff, but you only spend a few hours a day with those things. So is it just about the satisfaction of knowing that something is yours? That mode of thinking is completely alien to me.
But it doesn't matter, because I don't think a societal order can be imposed. It has to be adopted. It doesn't matter how vividly you detail another way of life if the transition isn't tangible and natural to people from their current position.
The sharing economies that have sprung up from the internet are a great example. They're completely counter to the existing order of capitalism, but they make sense from the day-to-day life perspective of people who are otherwise still living in capitalism. When you put the tools in front of people to conveniently both contribute to and take from a freely shared resource pool, the internet has proven that they don't need any special encouragement to do both.
You forgot a third component: Structuring and prioritizing said information. A huge infodump is worthless: Wikipedia without links would be a perfect example. Sure, one could try to get the collective to do the structuring, but then you'll run into the problem that the 'uniting goals' usually aren't that well-defined when it comes to the details.
Information can be structured organically by collective input without the need for manual guidance. Every social media network already does this on massive scale. Nobody's bothered to make one that's geared towards facilitating practical exchanges yet. We have software that essentially builds communities. Now add functions that help those communities to make collective decisions and work together. It all exists already in separate components. No one's put forth the effort yet to combine Facebook, LinkedIn, Craigslist, Reddit, and some basic consensus tools to see what happens. I bet with widespread adoption, you'd see it replacing the functionality that capitalism and government currently offer.
Leadership, which is the interpretation and adaption of said uniting goals, turning abstract goals into concrete commands and orders - or guidelines and practices, if you want a less militaristic rhetoric.
I think leadership is something that arises naturally or something that can be imposed, and I think it's only necessary to design for leadership in an organization if it's going to be of the imposed variety. I don't understand why you believe leadership is necessary for any of the functions you've listed, unless we have conflicting ideas about what leadership really means, which is likely.
and our ability to communicate today is completely incomparable to our ability to communicate more than 20 years ago.
Again, don't underestimate 20th century bureaucracies. This smells like hybris. (IIRC there were similar utopian ideas floating around during the revolutions of 1789 and 1917 - it's hardly a new phenomenon. The rule of thumb remains: We probably aren't that special.)
I think this works both ways. There are always people saying that things will never change, but they always do. I'm basing my assertion on precedent. Social revolution and communication technology revolution have always coincided. We're absolutely in the middle of one right now, and there are already big changes happening. The only question is how deep those changes can go, and how we will direct them.
We have the potential now to organize in ways that have never been possible before in history.
What ways? Quit using abstract terms and get into the details! Unless you provide plausible examples, this is a mere assertion.
To share information instantly and globally on any scale! To combine and filter the information from any number of inputs of any depth on any number of questions. Big data. Memetic culture. Stand-alone complex. I have the majority of mankind's collected knowledge tucked in my pocket every day, and can instantly fact-check anything anyone says to me. I can interact with people in so many ways that have never been possible before, including what I'm doing right now. An internet video recorded and uploaded by one person can turn into a thousand people rioting in a matter of hours. Or it can make them famous to the entire world in a matter of days. A small publication normally only read by a few thousand can suggest an action that goes viral and explodes into millions of participants around the world in a matter of weeks (Occupy Wall St).
You can argue that our existing structural paradigms still can't be replaced to any satisfactory effect, but it would be just weird to act like this isn't a very different kind of world we're entering into.
How does the ability to communicate faster make those 'shitty workarounds' obsolete?
Because all our organizational paradigms thus far have been for the purpose of gathering and disseminating information to a population indirectly. Information was passed up through a hierarchy, and decisions flowed back down. Because there was no effective way for large numbers of distant people to share information with each other and make collective decisions. Now we have those capabilities. It's not just about communication faster. It's about communicating with any number of people in any number of various locations all at once, and being able to receive and digest information in sophisticated ways from all of those people as well. It's a kind of social agility the world has never had before.
The mere existence of the internet doesn't provide anyone with an incentive to do something.
And what incentive do people need? If people want something, they'll work for it. If they have to work together, they'll work together. All capitalism does is influence what people work together on, and how the benefit is allocated.
(I also don't know why you call those workarounds 'shitty' - they appear to have worked out pretty well, haven't they? At least in Europe - that America is such a shithole in some places is hardly the fault of capitalism, but rather of the English because they drove all those religious nuts out of the country and to the colonies.)
I refuse to judge a system that operates by a network of global interactions by how well it serves a small region. Plus, human beings have only managed civilization for about 2% of its history, and it's already on the verge of destroying itself via the environment. I don't call that very successful.