GarethC
Donor
I think the answer is no, it's neither possible nor worth it.One of the major failures of the Pearl Harbor raid was its failure to destroy the infrastructure and ability of the US to continued to operate from the facility and repair the sunk/damaged ships.
Short of a full-scale invasion of Oahu aimed at "permanently" occupying the island (which seems a logistical impossibility in the long run) would it have made any sense for the Japanese to consider landing sufficient forces on Oahu temprarily to complete the destruction of the harbor facilities, oil depots, "sunken" but refloatable battleships, sow mines and block the channel in a way that would render Pearl Harbor completely unusable for a long time? Even if this was a one-way mission with surrender or fighting to the death the intended end, would this be worth it? Or possible?
Japan is critically short of uncommitted troops and sealift for a Dieppe-style raid in Dec 41, as it is already trying to take the Philippines, Wake, Malaya/Singapore, and Hong Kong while holding Indochina and not disengaging in China. Many of the troops intended for those operations are already double-booked, as they are intended to be withdrawn from their initial targets to take part in the successor attack on the Dutch East Indies. The DEI is the single most important goal of the initial war plan - without the oil from there, Japan will lose the war by running out of fuel for its ships and planes within the year. Jeopardizing the DEI campaign by risking a division and the transports to carry it to Pearl seems like a poor trade, and a worse one if those troops don't come back.
And that ignores the strong likelihood that Pearl's defenders would slaughter such a force. There's a big difference between getting an airstrike to hit PH and sailing fat slow targets like troop transports right up to the door, past all those destroyers and cruisers which weren't targetted in the air strikes.