To me (a non-expert) it feels that we have the same problem as land use. Vast unused lands are just sitting there fenced, while some other parts of the town is crazy crowded.
Of course, IP address might not have the same physical boundaries, but instead they have organizational barriers, which can be equally tricky ones, if not trickier.
The bottom line is that we suck at resource management and distribution at nearly every field.
The answer for land was property and inheritance taxes so families couldn't just sit on valuable land non-productively forever.
If it cost $1/year*address most entities with a /24 or /22 would barely notice, but HP might decide that they don't need 33.5 million IP addresses after all.
The problem is that the growth of the internet is up to now exponential. Even if we can get a few more years by spending inordinate amounts of money on reshuffling IPv4 addresses, it won't solve the underlying problem. It'll just delay the inevitable IPv6 deployment.
I've been reading about imminent address space exhaustion and the pending switch-over to IPv6 since I was proud of my five digit slashdot ID. It's easy to get cynical about it.
Oh, for sure, people have been warning about it for almost 15 years now (got my first tunnel in the early 2000's). But the difference now is that we've actually reached exhaustion, so I don't think it's fair to say nothing has changed.
Of course, IP address might not have the same physical boundaries, but instead they have organizational barriers, which can be equally tricky ones, if not trickier.
The bottom line is that we suck at resource management and distribution at nearly every field.