Moving up to a Baron

I will fully admit that I have several steps to go, so I don't want it to sound as if I think this is something I will accomplish soon. Rather, I am trying to identify the best path.

A little back ground...

I am 36 years old and grew up at the airport mainly around sailplanes. I soloed at 14, and got my private glider license at 16. I have about 100 hrs of sailplane time. Went to college and did very little flying after that time. Last year I picked up my SEL private and I have about 150 hrs of "airplane" (power) time. 250 TT. I recently finished my instrument rating. I have about 55 hrs Complex time in an Arrow and about 100 hrs. in 172's.

Here is where things get interesting. My father has an A36 and I was working towards flying that and I thought we were getting to where we could see the "light at the end of the tunnel". He has about 2,500 hrs. and has just decided he wants to move up to a 58 Baron. I see "the light" dimming and fading out.

Insurance drives a great deal of this, but, of course, practicality and safety are even more important.

What is the next thing to do? Should I fly the Mooney at the local flight school and just build complex time? Or, should I get my MEL and try and build multi time? Why does it seem it might be easier to rent the local Cougar or Travelair than it is to get covered in a Baron owned by a family member ?

Yes, any experience is good, but what are some of the best options as far as the next step?

Any thoughts appreciated.

RC