> It seems like once a group of people have lived somewhere for a generation or two and have a $Trillion invested in a place they probably are going to make it hard for new comers to make radical changes.
Few if any of them actually invested that money. Rather they bought when it was cheap and then sat on it (either individually or as a family passing it down through inheritance) as the price went up - worse still they vote to grandfather in cheap property tax rates for people who bought early, so they're not even paying their fair share at the most basic/direct level.
> Find a place people don't already want to live and make that better with great new housing designs?
In today's vetocracy that's pretty much impossible - you'd have to find somewhere where not a single person already lived. Even then, as soon as you started doing it someone would move in and then block you. (Set a rule that requires development to continue? There's already a statewide rule that cities just flaunt)
> Why do does someone deserve to move somewhere new and live there cheaper than the people who already live there?
Being able to move in at the same price would be plenty. Up until the '50s people moved where they liked and build what they liked where they liked, without any permitting or anything. Now it's illegal to build practically anything - the vast majority of housing stock is only legal because it's grandfathered in, and would be illegal to build anew.
> Now, that said there are huge distortions to the market driven by taxes and leverage. Many expensive places have 10% unoccupied housing. Think about how much that is. Imagine the time, cost, and disruption to build even 10,000 units of housing, when there are 40-50k units unoccupied.
Unoccupied housing is a scapegoat. A healthy market needs some liquidity. If you legalise building new houses then unoccupied houses cease to be a problem.