You might want to check out VoluMill's website, they have a free web-based version of their software you can upload a pocket profile to, and it will generate G-code using their high-performance strategies. I think it's meant mainly for evaluation, but it might be enough for some of your uses.
My other thought would be that you might just want to look at a good basic CAM package like Dolphin, BobCAD, even CamBam might be an improvement. This won't automate the whole process, but could maybe cut the time in half or less as what you're doing sounds like a *lot* of workarounds to get somewhere. My thought for how to do a pocket would be to manually pack the pocket with circular or elliptical pockets for roughing and then run a profile op (on the inside) for finishing.