I don't have an answer for you, but I'll be interested in following your decision, because I'm in a similar predicament. I, too, am relying on a mid-2009 MBP. I upgraded the memory and OS as far as I could go, but I've got compatibility issues with my other Apple platforms. For music, I run Band-In-A-Box and Reaper. I've been limited by the fact that my MBP only has one audio port, which can be used for either input or output but not both at the same time. Makes recording a little awkward, so I started using a Zoom R8 instead, and I just import the files into Reaper. It's actually a lot easier.
I've looked at the iMacs pretty closely. I got put off of the 21.5" model, because the memory isn't user upgradable. The 27" model is a real beauty, but getting one properly configured runs up the price pretty quickly. I also don't like the fact that an iMac glues me to a desktop. I don't don't move around as much as I used to, but I still like the portability of the laptop. Regrettably, getting one of those properly configured runs the cost up even more quickly.
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