PhilH - it seems like you
PhilH - it seems like you understand the message of heating the core to heat the feet and hands, so...
Yes - there is a way to warm up your feet before going on the run. Bundle the heck up indoors. Put your down on and a hat and wait around until your feet and hands get hot like bricks. This may or may not work for you, though. Personally, I wear socks for the 1st 1/2 mile. After 1/2 mile, my feet get really hot and I take the socks off.
Based on where you are at, though, I think you may need to just suck it up and get some minimalist shoes for the winter.
As for long-term expectations, from what I remember last year, it seemed like almost everyone was able to run comfortably in the upper 30s (barring those with Reynaud Syndrome), a good number of us were comfy down into the mid-twenties (myself included), and a scant few were happy into the teens. I live in Massachusetts, so very similar weather to you, and I need to footwear on the colder days, but it is less often than I anticipated.
Don't run on numb feet. I guess we can't say that enough, right?
And don't worry about my precious piggies, Longboard - I carry Smartwools when it drops below 40, just in case.