more cream seems sorta like too much cream and would negate the improvement of less oak.

I do agree. I thought with a backsplash and different paint on the walls that could help. I Would like to do an antique blue or gray on the cabinets, but I'm not sure how that would work with the tile. I also don't want the colour to get outdated.

I really like the idea of either white or light gray cabinets... If light gray, then it's pulling the gray from the living room in and connecting those two. (I agree, cream is too much cream) Then with gray cabinets, you maybe wouldn't feel that you needed to change your countertops, but for sure you can add some interesting hardware...

For the backsplash, you seem to have a transitional toward contemporary style... how about a glass subway tile?

I'd either do chocolate lowers and creamy uppers, or paint the inner face cream and the outer rim chocolate. I'd put larger pulls on the cabinets, and bring in backsplash to match the green you have in the living room.

Getting a bid on this from a re-finisher shouldn't cost you anything and might give you some ideas on how to do this. Hayleydaniels is right, this is a lot of work especially with oak! Oak is not meant for paint and can require some special prep work to make it look decent.

Painting isn't as hard as it is labor intensive. I've done many kitchens :) Personally I would go grey. That will pull in your family room and blend well with the tile and counters. I just did our kitchen with grey chalk paint. Here are some before and after photos.