I have seen worse--but since you are talking gut renovation, call in an Architect or interior designer with kitchen experience.

you should put this in design dilemma you would get more responses

I would say yes to all your thoughts, but you are not changing anything structural (not a 'gut) so I see no need for an architect. The extended countertop is a great idea. It doesn't have to match what you get for the kitchen counters. Take away that useless island, and look for a great central light fixture. You could put pendants over the extended bar if you like. The cupboards will look great painted, and maybe some crown molding just to give them a little more personality. Go for it.

Cabinets look like the biggest dilemma to me..change out of doors at least will give you much more flexibility in making your design choices...if u do not have an overall plan and are working slow steps on the project simple doors will not dictate your direction . The island is an obvious elimination...