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I'm on my second Skymaster, have a Master's degree in mechanical/aerospace engineering, and fly my aircraft out of Miami over the Caribbean. I generally agree with Kevin's responses, but would add the following.
On Q2, I'd always heard that the electrical systems were weak, but a British A&P who knows the system well feels otherwise and my two aircraft nver gave me a bit of trouble, so Kevin is right to say that you can manage with proper maintenance.
On Q3, my 1973 337G has 125 lbs of fuel, but since it's normally aspirated you can lean it per the POH and get 6 hours of flight. Who wants more, considering potty breaks and food?
This, by the way leads to another question: why a pressurized turbo? Makes sense over tall mountains, but for the Caribbean I think a normally aspirated is perfect.
On Q5 my opinion is to not get an A/C. I swelter at times (especially in Nassau, where the taxiing at times seems interminable) but if you're on the ground for any length of time the rear engine will overheat (simple solution: taxi with the front one if there's a long line, and start the rear when you get closer to the runway) and if the taxiing is short then it'll get cooler as soon as you get some heigth.
Ernie
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