Like you, I have oak (a little darker than yours) and want to go to Cherry. I have been having trouble deciding. Looks like you have enough natural light. Keep in mind that Cherry does darken some in time.
I like your wood floor. Is it oak? That's another problem I'm having. Trying to find flooring that will go with the Cherry and the rest of the oak I have in my house.
I hope to use the Choc stain on the Cherry. My cabinet maker does not offer that color but I'm going to see if I can get him to use it. It's seems to be a hot new color.....dark but still shows the Cherry grain really well.

Where do you want to go with the rest of your house? I think your woodwork is lovely, but by the looks of your furniture and accessories, you're heading towards a more modern look for your home.

Since you're already removing the beams, have you considered painting your trim? Normally my knee-jerk reaction is to gasp, "no way!" when someone wants to paint their stained trim, but painting the trim white/offwhite I think would give a more modern look to your house and give you more options to do what you want with dark cabinets.

My flooring is red oak, and I think it looks great with my dark cherry cabinets.

Actually, for modern, I'd go Peppercorn with stainless steel accents.

My floor is a character grade red oak and from what I have seen it works well with cherry and other woods because of the color variation.

My husband would have a heart attack if I painted the trim -trust me I want to.