I would think you would be best advised to talk directly to your insurance carrier about your insurance questions, as related to your hours. Otherwise you may make a decision based on bad information. Maybe you can apply for some Tarp money and get a deal on AIG insurance
As for P, T or NA. I think the real quesiton is, what do you want the plane to do. In other words if the T or P don't offer you anything you need (like high altitude cruising, for either long distance or mountain flying) then one would have to wonder what you would need the extra expense, maintenance and weight for.
My best freind has a new Mooney Ovation and he took off from Craig (jacksonville) 10 minutes after I took of from St. Augustine, and we both went direct to Key West. He cruises at 190Kts and I cruise at 155kts. He typically flys in the 10k area and I like 5k.
To make a long story short, they vectored him out wide for me to land ahead of him at KWY. So for a 325NM trip, we were within 10 minutes of each other, and he burned almost as much fuel.
So I believe that while it's cool to have the extra "stuff" I also believe that unless you need it, the extra stuff may cost you more in the end, than what it is worth. Again that's why I decided to sell my Turbo Navajo Panther and specifically looked for a non-pressurized, non-turbo 337. It seems to be the best plane for the money for the average east coast flyer (if you can find a good one at a good price).
And last but not least, becuase I don't get to fly a lot, I feel it is much easier to remain current in a non-complex twin like the NA 337.