Exactly how many times has Tokyo been destroyed and rebuilt?
...So a total of - 33 times
At what point will Japanese insurance companies wise up and stop writing coverage for monster-inflicted damage, thus rendering Tokyo un-rebuildable for financial reasons?
When that time comes, will monsters begin attacking a different Japanese city, or will they limit their depridations to the area formerly occupied by Tokyo, which will presumably revert to wilderness or become an encampment of the homeless?
Only a few films have touched on this aspect of giant monsterdom, Godzilla vs. Biollante had characters discussing the rebuilding efforts after Godzilla's rampage in 1984(1985 for American audiences) and even featured characters sitting in the "Godzilla Memorial Cafe" where a giant footprint rammed through concrete was used as a decorative skylight.
Tokyo wasn't always attacked either.
Rodan's rampage took place in Sasebo/Nagasaki. Godzilla destroyed Osaka and Hokkaido in Godzilla Raids Again, and the final showdown with Kong took place in Osaka in King Kong vs. Godzilla. In some cases the city is barely damaged during the monster fight, such as the final battle between Kong and Mechanikong in King Kong escapes - One building + Tokyo tower, the rest of the city remained intact.