You can always get some neoprene shoe covers for keeping your toes warm in winter with summer shoes on.

Sole stiffness to me is important in preventing hot spots. But if the upper doesn't fit then it won't be comfortable. I have some Bont A2s that are extremely stiff, but not super comfortable. My Sidis were more comfortable but not as stiff. My Mavic MTB shoes for riding cross are the most comfortable shoes I own. Were I in the market for road shoes again I'd go with Mavics. Get shoes you like at this point. The pedals can be swapped out if you have range of motion issues or develop hot spots. Pretty much any off the rack shoe is going to be compatible with any current pedal.