And while the quality of life in Boston could definitely be improved, the oldness of the city is one of the things that attracts me about it. Old things are rich and comforting. New ones can be somewhat bleak. Not just because old things have a patina. Old things are more human, because they tend to be smaller and handmade, instead of just extruded from a factory somewhere.
There is a great feedback loop here too. People that like things like the Public Garden are more likely to demand changes keep the feeling.
Even the Big Dig, while a bullshit waste of public resources, turns out to make the city much more pedestrian friendly. It largely emerged because the city was too old to retrofit a freeway system that could handle the capacity above ground.
There was inexcusable corruption and incompetence in the construction though. That puts of a taint on large municipal projects generally.
From what I've heard, though, the old highway was designed the way it was because of corruption too. The palpable aura of corruption in Boston probably doesn't help it as a tech hub. Corruption tends to yield low quality of life, because so much of the money that goes into the government goes to political supporters rather than into beneficial projects.
I've noticed practically all very corrupt cities (Syracuse was a striking example) are economically backward, though it's hard to say which is cause and which is effect.
All governments funnel money to their employees and supporters. For us subjects, what matters is that the rulers are competent and think for the long term. If they are smart and optimize for the long term, they realize that the best way to enrich themselves is to grow the pie, not to gobble it all up. The guys who ran Tammany Hall understood this, more recent corrupt rulers like Detroit's Coleman Young did not.
I don't think rule by corrupt political machines is ideal, I'd prefer if it if cities were run as joint stock corporations. But despite its many shortcomings, Tammany Hall and its ilk were much better at ruling than most of our modern city governments. Compare how the recovery of Chicago after the great fire to that of New Orleans after the flood. Or compare it to the (non-existent) rebuilding of the World Trade Towers. They were building infrastructure at amazing rate, we are letting it decay. If I could trade the current Boston government for Tammany Hall, I'd do so in a second.
This is exactly the wrong thing to do. You end up with a sterile wasteland.
Old buildings and a place with a long past (which in North America means hundreds of years) is probably great for the idea industry, as new ideas are built on top of older ideas, recursively. Having architecture around with a long history brings attention to this longer timespan, and provides the necessary perspective.
But for startups, it sometimes seems to me that the "blank slate" aspect of much of Silicon Valley encourages focus on the new and the future, which is pretty much what one wants in the startup space, as opposed to the idea space.
Old vs. new is just a matter of taste. The overriding value is whether something works or not. In general, the technical people I've met have very little patience for things that don't work, regardless of when they were built.