Well, thought long and hard as I could with limited knowledge I have about it all, but the consensus here seemed to be just bite the bullet and get a 4WD, so I did.
Since towing a boat up a wet ramp was a concern, thought about a V8 2WD with the "Auto LSD" but reading up on that showed it to be just a rehash of the VTRAC using the brakes to mimic a true LSD. A true 4WD V8 is about as rare as conservatives in Hawaii, so the search for a later model V6 was back on.
There was a 2007 Sport and 2008 SR5 available on this island for about the same, a bit under $20k. Both about 70k miles.
Since buying something from another island and shipping it over seemed like a $$$ cluster f**k, we went and looked at the 2007 Sport 4WD. Hour and a half of driving vs. dealing with TSA, renting a car, etc. to inspect a car was not such an attractive prospect. More than a bit less expensive as well.
The cosmetics could have been better, some TLC is needed, but mechanically it seems all there. Liked the idea of the bigger brakes on the Sport. No other fancy electronic gizmos, but I usually see that as stuff that craps out and it too expensive to repair. Who really needs powered seat memories anyway? Rear ride height control might have been nice.
Bought the thing and drove it home. Now to sell the 2001 2WD SR5, which is in better cosmetic condition, thanks to being a wife's car and lightly used.
Suppose this means I have to go live on the 4th Gen forum now?