A wise and experienced instructor in Oz told me some years ago to "wear the boots you can walk home in."
He had a point with the kind of country you fly over even 50 km north of Sydney. To make the point he had in previous years got a trainee, wearing the male equivalent of Jimmy Choos, to land in a confined area 2km from the school and on the pretense of checking a panel catch, left the trainee to walk home. If you are training people for the bush, you better train people for the bush.
I wear the Oz RJ Williams with leather sole which work well in all but the highest of temperatures. I've tried Timberland type Vibram soles and they are OK for experienced pilots but I would discourage trainees from them, for the feel points mentioned in this thread.
Perhaps the most important point about footwear in light helicopters? Is the sole dry. I have seen several pilots of light training helicopters on wet days, walking across the grass and then on lift-off having their feet slide off the pedals, to the alarm and despondency of the instructor in the left seat.
So keep a synthetic rag around to dry off your soles.
And rtnewboy, your've certainly struck a chord with your subject, as you see from the length of the thread. So remember, there is no dumb question...