That is not oak it is all pine (windows, stool and trim).

Maybe the windows I guess. The trim is oak though.

It looks good if there’s white trim but the sashes and doors remain stained.

If you want painted trim, paint it (or better yet, pay to have it painted) This trim is neither historic nor precious.

From the looks of the the small snippet you show and the coloring it is not oak. It is the same color as the window sash themselves and oak would normally look much different right next to pine.

Whether it's oak or pine is irrelevant. I agree with Hallett, paint it all white, it will brighten up all the rooms and feel fresh and clean!

Thank you all! And Hallet & Co… your comment made me laugh so hard because it’s so true! Thank you for such an honest and great comment

Any recommendations on painting them? Pay a professional? If we are trying to cut costs, is it worth risking doing it myself?

There is no 'risk' to doing it yourself as long as you follow all the annoying steps- clean them, sand them lightly, prime, fill any holes or dings that show up, sand lightly, spot prime, caulk, paint with two coats... Only you know your patience level- I write a check for that kind of painting

HALLET & Co, any recommendations on tutorials that you know of? I’ve looked on YouTube previously but didn’t find many of value. Thank you again for all of your help!

Two kids under 5 and white trim don't mix well in my world. Obviously, YMMV. :) I'd consider getting it professionally done either way because it's always a bigger job than it looks.

It is pine, not oak, but, it is nice pine and its well done, and I see nothing at all wrong with it. You dont want to change it out, and you dont want to paint it, and hiring it out would be expensive. Just leave it the way it is. It looks nice, and a lot of people really like wood trim. If you decide, it just has to be white like everyone elses, then, find a painter that specializes in trim, and make sure, he/she uses proper primer, and at least 2 coats of good quality paint. Also be aware, you have little kids, that may be bumping toys into those baseboards and door casings especially, they wont stay as pristine with paint, as they do with the stained wood. Make sure you have paint left to touch them up, because, you will be doing that often.

This isnt hard, just tedious and time consuming (that’s why it’s expensive). Prime first then 2 coats of paint.

I raised 4 kids in a house with all white trim. It can be challenging at times, but as long as they aren't riding bikes, playing ball, or roller skating in the house, you should be ok!

I love wood trim on windows. I say keep it. if the baseboard trim really is oak and doesn't match, go ahead and paint that. but keep the windows, they're beautiful!