Errant: gorgeous!!! I used a both caulking and wood putty depending on the type of joint/hole filling. I had recessed panels and at the point of recess needed caulking. Sometimes the paint will fill small gaps, but you really don't know how well until the caulking/filling phase is done. So it's just as easy to do it up front and be sure. I didn't caulk around the inside of the doors, but later I wished I had. Those paint gaps annoyed me even inside. I think I may have gone back over them afterwards. I had no shrinking or caulk issues at all in 4 years (then I moved). I think because the wood is 25 years old, it is very stable. Maybe with a lot of humidity, it may be an issue. Also be prepared that with white cabinets, they do show dirt easily. It amazed me to realize how dirty the wood cabinets were that I never saw. No hiding anything with white! I used BM Aura paint which was very durable and held up great to frequent wipe-ups. I also kept a small bottle of touchup paint handy. (Michaels: 2oz flip top plastic jars) Now BM has Aura Advance "cabinet" paint so either it's just a marketing change or presumably is even more durable for cabinets.

Have you looked at LVT tiles and wood look planks? I really think you coukd do wood look BUT there needs to be some contrast with your cabs. The fact that everything is the same shade is an issue to my eye. There are so many LVT options, and they will not raise the flooring height from that of the existing flooring.

Here's a picture of it next to what appears to be honey oak floors and it looks nice: Edgecomb Gray (Kylie M Interiors) Definitely try a sample of it in your space and look at it on different walls at different times of day to see if you like it in your lighting with all the other elements in your space. In my lighting the paint chip tends to skew a little purple, but I haven't heard anyone else mention that. I prefer Alaskan Skies (BM-972), which is very similar to Edgecomb Gray but doesn't skew purplish to me. The guy at our paint store tried to tell me Edgecomb Gray was the same color as Alaskan Skies, just a different name (they no longer carry the Alaskan Skies paint chip in our local store), but I can definitely detect a difference.

I think you can keep the trim oak and paint cabinets a color if you want. I like that idea better than painting trim in some rooms and not others. My opinion. trim consistent. Cabinets whatever you choose.