Could you post a photo of the room, so we can see the kind and number of windows?

Painted all the trim here including the outside window trim and left the windows stained dark. It looks fine to me . As I have posted here before the worst thing I ever did to a home was paint over the stained trim. I miss the look of the wood trim and if you have kids and pets the paint on high traffic servace areas like doors and baseboards constantly needs cleaning and touchups. Hopefully you won,t have those issues. Looking at new homes a few years ago and noticed alot of them have stained extended lower wood trim and the rest is sheet rocked and painted

My apartment is the same - decorators white baseboard, crown and doors. All windows - they are oversize - are a stained wood trim, no white. The windows were replaced some years ago by our building and it never ocurred to me to paint over them. I think it looks nice and as mentioned, upkeep is easier.

LOL I figured photos would probably be needed, I'm not great at explanations.

This is the hallway, the pic doesn't show all the doors, the darkness of the trim just really got to me after 5 years and the doors/door trim aren't in the greatest condition, the house was built in 1966, we are the second owners, most of the house is still in it's original built state. The trim and doors have a lot of scratches and poly drips from whoever originally finished them.

The dining room area, after we installed and finished the hardwood floors, the floors have evened out a lot since this pic which I'm kind of sad about.

What the windows look like up close.

This is an old photo of the living room area after we moved in, you can see the size of the windows are really nice.

This is a mock up of the living room/entry room space and shows sort of the built in plans between the two rooms that will serve as storage and separation in place of the common railing that is used in splits, most of the storage is on the entry side (which is how we wanted it) Built ins will be white with a wood top to match the floors. We're no longer going with the planks on the ceiling or all the way up the entry wall instead we're thinking a white thin depth coffered ceiling to hide the swirls (that I'm not a fan of) and wainscoting only in the small entry area underneath the built ins and around the front door going down the steps to the lower lever.

Last two pics are the start of building the built ins.

Two closed cabinets on each side with the middle one being open shelves.

All of my trim, doors and windows are painted. It's not too much white. Unless the wood/trim is really spectacular, I prefer it to be painted.

Since you are painting some if it, I would paint it all. But since you are unsure, can you paint the parts you are sure of first, then see what you think before painting the window trim?

Just my opinion, Nicole on Rehab Addict would never ever paint the trim in the houses she renovates, those houses are historic often and craftsman type, she sticks with the original stain if at all possible. Your house is much newer, paint them if you want to and do it happily, just be sure to prepare the wood properly and enjoy your hard work!