NY, SF, Boston > Every other city in America
I'll admit that those cities are not for everyone, but they are irreplaceable for most people that live in them. If you make enough money to live in one of those cities, the lifestyle cannot be replicated outside of those cities.
VCs can choose where they want to live, most of them choose tier 1 cities. Talent also chooses tier 1 cities so the collocation benefits everyone.
The Midwest is the perfect place for a startup. Now that being said, Chicago has an entertaining startup scene. Entertaining in that I feel like they are trying too hard to be like San Franscisco.
What about Chicago? Great city, not as expensive; problem is, not much VC money. I would rather the worst thing about where I live be called "January" than have it be called "rent".
VCs can choose where they want to live, most of them choose tier 1 cities. Talent also chooses tier 1 cities so the collocation benefits everyone.
Talent doesn't get as much "choice" as HN likes to believe. Sure, good programmers get solicitations for jobs all the time, but often that's just an invitation to waste time on a phone screen, spend six hours on a code test (because you actually care about doing things right) and then get rejected because your choice of language (for the test) fell on the wrong side of that company's ever-shifting internal language wars. Or it's an invitation to work at some startup with shitty cargo-cult culture that'll fire you at 4 months with no severance if you don't go to the strip club with the other brogrammers. Good jobs are goddamn rare and hard to find no matter who you are.
Talent should have the kind of leverage that HN believes it does, but right now, 90+ percent of talented people are poors who still need to adapt to bosses and market trends and landlords.
Also, DC is pretty good too.
Arguably, NY and SF are far better than Boston, and you could probably safely lump Boston in with Chicago and DC as far as desirability.
I agree with you that talent doesn't have as much leverage as they think they do. Good jobs are nearly impossible to find. That is why living in a great city is so important. Talent will never have the type of leverage HN believes it does except for in rare individuals who have built social credit along with their skills.
Now that I'm almost 30 and aware of my mortality (my mother passed away recently, which had more to do with my "mid-life crisis" than chronological age, since I'm still quite young by the standard outside of Wall Street and VC-istan) I'm starting to wonder about the best way to change this. How do we take this garbage-pile of an industry and fix it? How do we clear away the crap and build something we can be proud of?
Social trends are such that we're on track for a violent worldwide revolution (widespread, permanent un(der)+employment will be the norm by 2030) unless we fix our society in a major way (basic income, necessitated by said underemployment) but we also have the tools available to be smart and not burn/kill our way to a better world. We don't need to overthrow the corporate bastards with force (at least, I hope we don't; the problem with real-world holy wars is that the unholy have guns and better aim) because with technology we can outperform them. We should take this opportunity to rewrite all the assumptions, if we can.
As far as your first question... who knows? One thing I know for certain, it doesn't matter what you do, or how you do it, there will be trade-offs, always. As a much older than you... 30 year old, I've come to sort of just enjoy what I can and brush off the unpleasant stuff while I keep up with a rigorous search for knowledge and improved skills.
I'm certain that opportunities will present themselves, and I'm positioning to always be ready to take advantage of them. Fulfillment for me partially comes from the knowledge and skills gained. I know that I will have a high level of achievement over my career and because I am confident it will all work out, I am relaxed while I push myself.
In 2 years, maybe I'll have a totally different outlook? I guess that is the fun of the whole thing.
Or it's an invitation to work at some startup with shitty cargo-cult culture that'll fire you at 4 months with no severance if you don't go to the strip club with the other brogrammers.
Chicago is ok but be aware that it's bro central if that's something you are trying to avoid.