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Bill is right, it's a good question. Here are some other points:
On the Skymaster being cheaper and using the savings to pay the higher operating costs, the math doesn't support the Skymaster. If you save $35K on it (the average of your numbers) and put that in the bank, it will yield about $1,000 per year (at 3%), which probably covers the maintenance differential but not the fuel differential.
I don't buy the suggestion that the Cirrus with parachute is roughly as safe as the Skymaster (you don't quite express it this way, but it's implied). In an engine failure right after take-off, I don't think the parachute is much help, and that's when engine failures are most prevalent (because the engine is stressed to its maximum, often when it's also going through the thermal transient from cold to hot).
I'm on my 2nd Skymaster (a 1973, after a 1969) and I don't agree that the later models are better, nor do I recall ever hearing that comment.
Finally, on the Turbo, my understanding is that, in addition to even higher fuel and maintenance costs, they are also significantly more expensive to buy. This, of course, under normal circumstances, which may differ if you find a cherry Turbo from a distressed seller. But if you have time to look carefully, you should be able to buy much more aircraft for the same price if it's a normally aspirated model.
Ernie
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