You can also sidestep 90% of the advertising problem without infringing on actual speech by doing something like saying that "billboard-like things on a property can only be erected by the property owner, and cannot receive remuneration for said erection".

Then the local guy can print "SHERIFF JOE SUCKS" on his fence without repercussions but large billboards are mostly banned.

You still have the gas station sign issue, but that's separate.