I would start with updated appliances and possibly a focus over stove. The counter tops and splash could be upgraded to a more current material and look.if you are going for a contemporary look glass tiles would look great. It would be helpful to have a plan so you could execute a cohesive look and do it in stages. I would suggest talking to a professional kitchen designer even if it is at a big box store.

There are many examples on houzz of contrasting counters for perimeter and island. For example butcher block on island and stone on perimeter or a solid color on one and something with movement on another. I would only mix two stones if one had movement and one was fairly solid. The stainless on perimeter and something else on island sounds good to me. Here is a pic of stainless counters with what looks like a stone breakfast bar. (I hope I understood your question right). http://houzz.com/photos/3137660

Yes, I understand. My own kitchen is similar.. What I like best about your kitch is that there are essentially no upper cabinets. This is a very modern concept, and although your kitchen is not new, it has a progressive design. You are constrained on placement of appliances because of the windows and walls, but that is all right,. I believe that the best outcome for your kitchen would be to swap out your old cabinets for new ones of good quality. I like the timber floor. I would use a simple countertop of thin material (not with a built up edge), keeping the overall feeling light.

That's a fabulous idea. I don't like that front board but it's lacquered to coordinate with the cupboards, so ot couldn't be painted . I could keep the stools and improve the hated kickboard. That would be a double win. Although a lower back would be nice. I kind of like those white lattice designer ones, would they be too busy?