How big is his house? How much is it worth now?

Property taxes are based on the assessed value of the land. So if you bought vacant land in the 1970s, improved it with a home, and then lived in it for the next 50 years, you'd see a piece of land that sold for several thousand dollars accrue to hundreds of thousands of dollars. If this guy is living in Texas, he's likely paying 1-2% of the assessed value of the home, which could easily be north of $2-4k/year. That's on land that was practically being given away half a century earlier.

Who does he think maintains road networks and all the other infrastructure he relies on?

The tax rate is fully disconnected from the cost of construction/maintenance. So if my house accrues from $50k to $200k over the course of ten years, I don't see 4x as much construction/maintenance of my local infrastructure. I just see my tax bill go up 4x while my potholes continue to go unfilled, my lines unburied, and my flood control underdeveloped.

And that's setting aside the habit of municipal governments to invest in "improvements" (sports stadiums, convention centers, police surveillance that's focused around corporate properties, twelve lane highways that induce demand rather than improve traffick flow) that benefit private industry over public welfare. City and state officials serving larger and larger constituencies routinely become disconnected from lay voters and increasingly complicit in graft and other kickbacks, as elections revolve more around partisan affiliation than any actual domestic management agenda.

There is a very real and meaningful disconnect between what politicians do at the municipal/state level and what residents actually demand at the retail level. If this guy was perched in a penthouse overlooking Cowboy's stadium, you could reasonably tell him to fuck off. But I guarantee he's not.