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HI,
There is nothing extraordinary about flying a naturally aspirated SkyMaster. If you are COMPLETELY comfortable in the SR20, then flying a naturally aspirated SkyMaster should prove fun and enjoyable. You will simply have two levers in your hands as oppossed to one and don't forget the landing gear. Insurance, as Ernie mentioned, will be pricey especially at your experience level but you either pay it or not. The choice is up to you.
When I started flying the Skymaster, the only multi time I had was what I got training for the rating in a Piper Seminol. So that number was 10. My total time was about 1500 with maybe 500 in high performance/complex. The Skymaster, in my opinion, is the perfect airplane to transition to mult-engine flying. It may very well be the perfect light twin in terms of aerodynamics. One has to start somewhere, the Skymaster is a great place to do it. I have over 600 hours in my SkyMaster now since beginning multi flying in 2003 and have no desire to fly anything else.
A MEI with Skymaster time would certainly be a plus but should not be a requirement. More important would be a competent one that you like. If the MEI does not have Skymaster experience, please, please, please make sure both of you know the systems backward and forward of the exact model you are flying. Model years differ alot. Pay extra attention to the fuel system and landing gear. Most of the sad record of Skymasters comes from lack of understanding of the fuel systems by unprepared pilots. Though the record for Skymasters compares similarly to other comparable twins, it should be better. The fuel systems have caught many pilots by surprise. Operate that and the rest of airplane as designed, and nothing but enjoyment will follow.
Good Luck!
Ed
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