Justin - thing is you could probably have made your post with regard to seafaring and supporting colonies in far off lands - yet today we are quite happy to ship shrimp from Scotland to China to deshell and then ship them back again to eat.
Seafaring colonies were always self-supporting - even if they weren't meant to be real colonies, like the Dutch settlement at the foot of Table Mountain which was set up as a resupply station for ships of the Dutch East India Company. Any shipping done today is done because economically it is
cheaper, not more expensive. My guess is that the labour cost of deshelling shrimps in China is much less than in Scotland, and more than makes up for the transport expenses.
The ISS is akin to that; a very high priced pioneer where the expense is likely far greater than the financial gain. Also don't forget that technology often hits plateaus for long periods of time before getting a new breakthrough. So spacefaring might well just be in one those spots whereby there aren't any big gains to be had, but where investment is required in order to keep making those small, important strides; some of which might lead to the big strides to make things more economically viable.
The ISS could never become self-supporting no matter how big you make it. Neither could a colony on the Moon or on Mars. They would absolutely depend on high-level technology that they could not begin to manufacture, and that would have to be shipped from Earth - indefinitely - at a horrendous cost. If you and every human being on Earth was prepared to pay, say, a 50% tax on your income purely for a Mars colony then perhaps it would work, for as long as the tax is paid. But what are the chances of that happening?
Technology does continue to advance, but notice how each breakthrough is more difficult and more expensive to implement than the one before it. In the 19th century individual inventors made great strides, creating the light bulb, the petrol engine, the telephone, the phonograph. etc. In the 20th century two men created the first flying machine. But after that, what did it take to create the first jet engine, the first nuclear reactor, and the first orbital launcher? Does anyone seriously think that an enthusiast, in his study, is going to come up with a technological marvel that will revolutionize our world?
Technology has natural limits. It's not through lack of theoretical knowledge that we are hitting brick walls. Our theoretical knowledge has far outstripped our ability to make practical use of that knowledge. We know all about antimatter but there is just no way of creating it cheaply enough to use as a viable power source. It's the physics: as we manipulate matter at a deeper level, going from chemical reactions to subatomic particles to changing the nature of those particles, it gets more difficult, until a point is reached when it just isn't economically viable to go any further.
I see it as a long term investment approach to science and research and advance. It's one of those things that is looking 50-100-200 years in advance rather than looking two or three years. Plus along the way don't forge that 0-G research does have direct appliances in modern day. I think that a lot of people forget how much trickles down from groups like NASA 0 mostly because most people are not involved in science and only cotton onto new tech when its made widely commercial (and we have to remember that what we get commercially is often years behind what is actually possible currently)
I'm not aware of any research on the ISS that constitutes significant breakthroughs either in theoretical or practical knowledge. There isn't really much more we can learn, say, about the effects of weightless on the human body that will substantially affect how astronauts will be equipped for future space voyages.
Don't forget its been 60 years of space; it took us hundreds of years to get further and many more to be able to build things like aircraft carriers and oil tankers - vast ships that would have, at one time, been utterly impossible beyond comprehension.
Sure. Aircraft carriers and tankers became possible once steel could be manufactured cheaply and in sufficient quantities to use for shipbuilding. It was a real breakthrough. Notice however that carrier technology, like every other branch of technology, has plateaued: the Ford class carriers are not dramatically different from the Nimitz class that go back to the 1970s. Space travel technology plateaued long ago. We can't come up with anything better than a rocket engine for getting satellites and humans into orbit. There were hopes for the Skylon, but it seems it will be more expensive than Elon Musk's reusable launchers, which, incidentally, are not as reusable as all that. Musk still has to prove his case, and even if he does it will never make space travel as cheap as commercial flight.