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Good summary. It looks like you've been reading the right threads (including "What to look for when buying a Skymaster").
I wouldn't disagree with your summary, but allow me to add a few caveats or clarifications.
Expensive to own. No more than other twins if you buy one that has been properly maintained. Regrettably, some new buyers get beat-up Skymasters that become very expensive to maintain.
Quirky gear. Same as above: no more quirky than other retractable gears if you get one that was properly maintained.
Quirky engine heat management. Can't comment on the 336, but this is not a problem for 337s in the kind of service most pilots will face. It is a consideration, and requires management, when flying out of crowded airports in summer heat. (When I fly out of Nassau, I start the rear engine on the taxiway when I'm second in line for takeoff.)
Other than that, you've got a good picture. I'm no expert on insurance, but I think a 336 will cost less, perhaps significantly less. Come to Miami and we'll go flying.
Ernie
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