Re: How about ...
"Sold" properly to the current .org users with an easy mass migration path you could kill the sale of .org instantly as all the profit is gone
The technical migration is pretty simple, ie changes to zone files. But there'd be huge problems for current .orgs, and costs, so cost of change to communicate their new URLs to their users.
I think the more interesting question is the risk of root fragmentation and alt-roots. So technically, you could take a copy of the .org zone file and encourage traffic towards an alt-org DNS. Then charge cost+ to register & renew at the alt-org. Basically a bulk DNS 'hijack'. Not sure what the legalities would be, but possibly just copyright for cloning the zone.
But that's a public good, right? And ICANN says it's ok because there's a 'market', which justified lifting the price cap. And an alt-org would achieve that, given the current problem is transferring the current .org monopoly to a for-profit entity.. And techincally, it is very feasible to break the TLD monopolies.