I would. SW Alabaster

Paint the walls, ceiling and trim all the same color. different sheens of the same version of white for a fresh look. egg shell walls, flat ceiling and satin trim.

The windows appear to be pine to me, the stain may make them appear honey oak. You show one picture and ask us to grade the entire house. I prefer stained windows and trim to painted so personally I would look to other options to "modernize" the home.

They probably are pine -most "standard" trim is pine stained to look like oak. I speak from experience :-) we have that same trim throughout our 1993 house and have debated for years about painting it all white or light to match our walls. Every person we spoke to during a 2015 remodel and recent 2022 replacement of all our windows said leave it alone. We had a fabulous local painting company who matched the stain color perfectly to stain all the new pine trim and window sashes the same oak color. I agree with millworkman, find other ways to spruce things up and I'd start with getting rid of the curtains and just leave the blinds. We have the same inside-mount cellular shades in all our windows, and it just gives a nice clean look.

It looks like you have really nice wood trimmed windows that were built prior to the trend to use cheap paint grade wood for all the trim.

Just looking at the one small picture I would say, don't paint the wood. Concentrate on the things in the room to make it feel more modern.

These rooms would not look benefit from the trim being painted white:

I would like to see a picture of a window in another room so we can see a whole window, not obscured by drapes. I will say the cost of having all this woodwork painted might blow your mind if you have someone else do it. If you do it yourself you will find out how time consuming it is. Maybe getting a quote for the work will help you decide. :-)

White or stained wood molding goes in and out of fashion, if anything I would say wood is coming back around, so I don't think it's a problem if you left it stained. The one that looks best also depends on the style of the house and we can't get many clues from one picture, so I don't know which is the best choice here.

IMO most 60's trim was not great so paint but I need a lot more info . Your decor looks very tradtional so is that the style you want for the home? Take more pics post here in a comment or two DO NOT start another post. Some clue as to whatever else you are changing and your plan .

Keeping traditional because thats what i seem to always go back too! light couch and rug dark wood accents! just concerned about windows and moldings!

The honey oak moulding isn't objectionable. I do agree with one of the other posters that painting your walls a brighter white would add more contrast and make the moulding pop more.

Thank you all! have lots to think about! ps: things are covered because we babysit and kids are always playing in the room!!