Whenever people see old systems still in production (say things that are over 30 years old) the assumption is that management refused to fund the replacement. But if you look at replacement projects so many of them are such dismal failures that's management's reluctance to engage in fixing stuff is understandable.
From the outside, decline always looks like a choice, because the exact form the decline takes was chosen. The issue is that all the choices are bad.
Also, traveling and routing utilities and police and ambulances and all of society around a larger plot of land costs (in time and energy and materials) at least a power of 2 more than a smaller plot of land.
Not only are there are no marginal tax rates for land value tax, but there are tax breaks for elderly, caps on tax increases the longer the land is owned, and tax deferrals (such as 1031 exchange).
I will leave it to the reader to figure out which “tribe” is most represented amongst land owners. And old people receiving Social Security and Medicare.
Treating this mentality of "taking money out that you put in" as "taking handouts" is the exact reductive mentality being used to try and have the government steal the money you earned from under your nose.
Means testing will also make paying into these programs even less popular. Upper middle class people will ask why, exactly, they’re expected to pay more into a retirement program they will get less out of. That’s a recipe for political change from a party who promises not to do that.