What a darling house! I think your kitchen cabs are pretty, and your kitchen will look great once you lose the red! I am not the best at paint & painting advice, but others on here are & can give you good advice. I think white trim will look fine with your cabinets. I think you could remove the awnings, but the one over the door serves a good purpose...keeping rain off of people entering your house. I'd probably wait to remove it until perhaps having the opportunity to build a porch or some sort of nice looking overhang.

You may want to paint the walls in your chosen colors and see how you like it with the wood trim. In the kitchen the trim appears to match the cabinets. If the trim is too beat up, or you hate it, you can decide on painting it later. How fortunate you are for having a new kitchen. Congratulations on your new home!

When painting wood you need to really be aware of the wear of a piece. Painted cabinets,tables etc. do not hold up if not done WELL. Since you are beginning this journey of home owning I would start with easy DIY--lighten walls, be sure ceilings are white..that will go the farthest to add light to rooms. Only you see the master bath. That is not a room I would spend tight budget money on. Go for rooms that are the most public, unless you are talking maintenance. Always put maintenance needs above esthetic wants. In the pictures your wood looks well maintained....give yourself at least a year before you take such a huge change on. That is one you cannot come back from. I wonder if given the age of your home if the original casings weren't white? Back in the day white was used to cover the cheaper wood choice on inexpensive homes. Someone put a HUGE upgrade when adding oak to your homes trim out. Painting it would be tragic IMHO.

Lighter colors on the walls would help brighten the rooms considerably. I, too, would leave the woodwork as is for now. Consider using a color, rather than cremes, light greys, etc. I'd choose a color such a blue (or anything that looks good with the cabinets) and use a very, very light shade of it on the walls. You could then use other, more intense versions of that color for accents (curtains, wall hangings etc) in the room.

Congratulations on your new home.

I think you can certainly paint the wood trim around the door white. Use a semi gloss and it will be fine.

I agree that the first thing to do is paint. I love neutrals, but with your light wood kitchen, which seems to have a yellow undertone, I would go with a light saggy green.

I agree with Arcy. Start with paint, and in the public areas first. It looks like the house was well maintained inside. How is the outside?

If you paint the walls in at least one or two rooms before touching the trim. White or pastel walls with stained trim is a very current look. That may be all the lighter and fresher you need, and it will be a lot less painting (less work and paint if you do it, a lot less money if you have it done). If the trim is something you plan to DIY, doing trim well is more work than walls.

As for the kitchen, I don't think you have to have kitchen cabinets the same as the trim, but yours matches nicely. I wouldn't rush to change it.

I would remove the awning over the window, but I wouldn't remove the one over the door unless you replace it with something else. Painting the shutters would be a priority for me -- maybe the door.

Things tat might be quick fixes or long term, - I would replace the steps or extend them to the width of the center section of the house. It just feels cramped to me as is, and the railing is completely utilitarian and probably a good thing to have, but I would look for ways to have something more attractive. And then I would work on doing some upgraddes to the flower beds to give them more texture, color and interest. That is often something that evolves over a few years.

The bathroom shelf next to the toilet... looks like you are going to have to live with the angled ceiling there, but you could put some shelves in that opening, put cabinet doors on it . I am assuming the bump out below was done to hide something mecahnical or has to do with the roof line, but I would double check that and make sure you don't have the option to open it up. You can definitely put doors on the shelves across the room.

I have white painted trim and cabinets and I would love to have your stained wood trim and cabinets. I also vote for painting the dark colored walls. You will be amazed at the difference that will make. You can always paint the cabinets and trim later. One of the big advantages to stained trim, windows, and cabinets is the way it is very easy to touch up a nick in stained and it will be very hard to find. It is much harder to touch up paint.

Congrats on your first home purchase! You and your boyfriend have got a very cute house. I am in agreement with others regarding paint. It will make a huge difference if you just paint the walls first. It's the easiest change you can make. Since you're on a tight budget, I'd recommend living in the house for a while before making too many changes.

What direction does your house face? The awnings may be serving a purpose in winter when the sun is low in the sky.

Thank you for all the help! Before this I did not even know oak was a hard wood to paint. I guess we will do the live-in, and see what we really want after actually spending time there. If nothing else, I'm thinking the contrast between a darker stain and light walls would look nice as well. I'd still like to hear more though, so feel free to keep commenting! I also love the ideas for the bathroom, especially replacing the tiled shelf in the bathroom with ship-lap. (I love Joanna Gaines!) Luckily, I think a good deep cleaning and some fresh paint will spruce up the house immensely. The extra bath downstairs was newly remodeled as well, so that's one less thing we have to worry about! Only sad thing is that when the previous owners painted, they did not tape the trim so it's all paint splattered :-( Thanks you as well for all the kind comments on our house. I am excited to make it into our home.

My trim at my last old house was all painted--bright colors and a different one in every room. It looked horrible and was a PAIN to paint, just due to all the edges, etc. So pick a neutral color and do all your trim the same color if you end up painting. That allows you to switch up the wall color if your taste changes relatively easily, if your trim is neutral. I used antique white for mine when I redid. If you go with really light walls, that will cause your kitchen cabinets to really stand out (ask me how I know). If you're not that crazy about them, I would pick a light COLOR (can be a neutral like tan or gold or brown or griege) that picks up something from the tones in the wood. That way the cabinets will stand out somewhat less. I wouldn't worry too much about that tile shelf in the bathroom, it will fade away when you get the place decorated and stuff put on it. If you really hate it, put a fake philodendron vine in a basket on that shelf and it will cover a lot of the tile.

There is a product called oops, that will remove the paint that is spattered on the trim. My daughter had a house where all the trim was splattered from a sloppy paint job. We managed to clean it all before they moved in, and it wasnt as bad a job as I thought it would be.

Krud Kutter will also remove paint.

I would leave the woodwork varnished rather than painted....vacuum cleaners mar up white woodwork or even chairs pushed up against the wood. Paint the walls light pastel colors that you like and you will notice a lot of light and airyness. Congrats on your new home. I have oak cupboards also and love them....so easy to clean and look nice all the time.

What a pretty house.

I'd start with painting everything a creamy white. Another favorite color is sw agreeable grey. It changes with light and will look different in every room

I would leave the trim as is and paint the walls a light neutral color. You can always paint the trim later. In my experience, it is always better to live in the house a while before making changes that are hard/impossible to reverse. If that is the original trim in the house, it is more important to wait and see how you feel about the rooms after you paint the walls.