Yes

Paint and remove that single chair rail that is cutting your walls in two.

IMO the first thing to do is get rid of the arched windows and as for the trim yes painting is the answer unless you want to spend 1000s on replacing. What is your style if at all close to contemporary those arches need to go. Since renovating is in the near furture why not just leave this trim issue until the end you might find that the windows are in the wrong place in some rooms even.

More pictures of your new home - inside and outside would be helpful. Also, what is your style?

What is your budget? Start with an overall plan. Will you be making big changes to the outside? New siding? (Removing and/or replacing ANY windows needs to be before that.) The window arches themselves aren't a problem - if they fit the overall style.

I can see the 6 panel doors in your photo. If you do decide to paint all the trim, maybe find a cabinet finisher who will use a grain filler and high end paint (Renner, Milesi, Envirolak, etc.), rather than throwing out solid wood trim and mouldings.

that's just wallpaper, not an actual millwork chairrail, right?

While the flooring is out, I would have a painter in to prime and paint it all, including the fireplace.

...while you live in a brighter space, dream about the reno you'll be doing when you can afford to do it right.

Ps, what’s going on with those marks on the ceiling above the fireplace? Is your flue broken?

Laura-before you do anything, get a firm vision of the style and direction you want in this home. Looks 1980-1990?
I would take steps that are temporary first until I had my “vision” nailed. So I would paint/stain walls and fireplace white. Leave wood trim as is for now. Changing shape of windows is expensive and requires work inside and on exterior. Big job. Here are some concepts. Look on Houzz for pictures using key words and styles you lean to. Save photos in “Ideabooks” here on Houzz. You can insert “notes” on each picture stating what you like about each picture. Do this because believe me you will forget over time. I like the idea of a high black rod with light drapery panels at each window. I would also get beefier mantel for the fireplace. Do flooring in wider planks engineered wood for more modern look and overall lighting. Invest in super great chandelier once you have nailed your style. Your “style” will immerse as you “save” photos you like.

I was wondering about that too Theresan.

You need to get that fireplace inspected and repaired if needed. Don’t use it until that is done.

Not knowing what style might suit you, I took a leap and pasted some ideas into your room. I pulled out the wet bar and inserted a free standing bar cabinet to better utilize this spot. White walls, Romabio white brick stain, light window panels with cool planters in front of windows to draw the eye down and distract from arched windows. I added beefier mantel. Repeating tone of wood paneled doors. That tues that wood in without surrendering to it design wise. A great rug, some art over mantel and chandelier would transform this room and give a great inspirational boost for your efforts.

I put this chandelier in the room. I used black to bring contrast and greater interest to the room. It’s a fun project for sure.

I would just paint and add drapery panels to minimize the arched window.

And the fun begins!

As mentioned, start collecting inspiration for the home.

I would actually paint the trim last. You may grow to love it. Wait and see.

As for the fireplace, most are inspected prior to actual purchase of the home, so you know what your dealing with. Well I guess that may only happen in some states.

I put that identical chandelier (42”) in our great room, but at Wayfair it’s only about $200 😜

Ableton 6 - Light Candle Style Chandelier
https://www.wayfair.com/lighting/pdp/birch-lane-ableton-6-light-candle-style-chandelier-w004939121.html

Theresen. Cool. The Pottery Barn one has a wider and lower profile shape which I like for Laura’s room. Mainly due to their ceiling height from what I can see. But your’s looks fantastic with your vaulted ceiling and $500 less cost is nothing to sneeze at. Nice job.

I would consider a chandelier that is more fun visually and casts some light which can be directed.

Here is a recent design we did for a client. Notice how we didn't paint any of the trim and it's actually highlighted as part of the home.

Mt. Washington Ski House · More Info

Mt. Washington Ski House · More Info