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When I was shopping for the Skymaster I spent some time checking out whether the weeping wing was possible for a Skymaster even on an experimental basis. Simply put, it is not. You are stuck w/ boots, hot plate, etc.
As far as your practical situation re: the Skymaster and insur etc, I got my twin rating in a conventional twin so I am legal in such. If you get your twin rating in the Skymaster, you are limited to the centerline thrust. Frankly that is not a big deal for me, I don't care to fly a conventional twin, however both the twin rating and an approved Skymaster school were required before the insurer would cover me. Also finding an approved instructor for the Skymaster in my area was a problem. All in all I am satisfied w/ my choices. Make sure you find a Skymaster w/o too much deferred mantenance. I bought one from a former member of this site w/ low time engines and supposedly a clean machine. I have spent 60k+ since I bought the bird. Much of that was planned upgrades but at least 20k was unplanned fixes for deferred maintenance.
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