Hi Cassie, My suggestions are most likely not what anyone wants to hear. However, I believe it is the important part before you paint. Generally, we paint the house, we paint a room etc. What we do not do is plant the entire home from roof to entry. I think the house is big, but is is missing a style. It can be anything you want right now. Perhaps you do a wall with stone or part of the wall in stone, and the rest in paint. It may take longer, but you will never paint again. I am suggesting you find a local architect to help you go through the steps and design it all now, it is a blank slating waiting for a crayon. There are other areas you should check prior to painting. How is the foundation and the lower level - it is below ground and I do not know if water can get in or has gotten in. I would do two things. Hire a very good engineer to walk the entire home, and make sure all areas are secure from the future snows, rain, mud season, and summer. ADT and other suppliers have a bug water device. This unit sits on the wall or in an area where is it dry, but might have had a leak previously. Approximately 18" off the ground. If the connection is hit with water it will break and alert you. In a home I worked on in the mid-west we had to take care of the foundation and the cold weather first. The little water bug is good to announce that water has arrived. The person you hire, might tell you, that you are great or you have areas that should be addressed. I have found doing this first is generally the best way, since painting the home and then having a bit of water, it means you are now diverted to another area. Not painting, but repair Repair is always more expensive than, making sure you do not have a problem. And, they might arrive and say you are 100% perfect. I think the bottom portion of the home would look great with a stone wall wrapped around it. The midwest has many homes with this and the look is not only grand, but not expensive to achieve. And, you will never paint again. Getting a pro to come out and do a concept of what you might do as you go along will give you the following: 1. On site advice and information. We are not there. Helping with drapes, wallpaper that is ok on line, but the real stuff you need a person to see what is there. 2. Planning now how you want the home to look and what you need inside and out is a great way to budget how you spend your funds. 3. Adding an entry that is substantial with a two door entry is a good idea for your area. It get's cold and one door with no outside door will let the cold into the home Picture walking up a set of steps 2 - the area is 10 feet wide, and you open a double door, 72". Step inside and on the right and left you can have a bench on one side, a 30" tall unit on the otherside. The tall unit can hold, boots, shoes, wood, items you might use outside. And a place for umbrellas, a place to put packages etc. You could heat the floor here and leave boots and shoes under the bench. The snow ill melt off and the inside stays clean. This newly added front I have at 10 feet wide x 12 feet deep. Now you come to the door into the home, it can be one door with glass above and door below or all glass etc. Folks leave their boots and come on in. The next area is the welcome hello and we have not seen the inside, but here you can tie the look from outside to in. So, if you did add stone, and the upper portion had a color, I would pick perhaps a deep slate grey. Adding shutters is great and they could be in Navy with a white trim on the window. So the color scheme is stone, maybe local. Grey (slate medium tone) , white trim and Navy for the shutters. The alternate flavor is not stone, all paint, big house for all paint. I would try and cut it in two, Perhaps a large wrap of ledge stone to designate 1st floor to 2nd floor. The first color should be a lighter color, pale yellow, and the upper color could be the cornflower yellow that is in so many flowers in the midwest. I would pull all my colors based on the area and what Nature has given you. The colors for the first section is as follows: Benjamin Moore Historical Color Hale Navy, Grey - Cement (horrible name great clean clear color, no blue in the grey just grey); the ledge stone is thick about 2" and is pure chalk white, the white is Behr Ultra White. I hope this helps, it is a start. My final words in this very lengthy e mail is houses take a lot of work, but planning ad doing small bites makes it easier. The other part is when you have planned it out - things become simpler. You know that in 2020 you will add in that big fireplace and the interior some. Or in four years it will be kitchen time and kitchens change so much just designation of space may be all you need. I hope this helps. It is not your standard answer. Houzz has many people available in your area, Cassie I hope you give it a try. One visit is a good place to start. Thank you for sharing your project, I wish you the best. A Coco I will drop in photos next.

Search "color block" in Exterior photos on Houzz for examples of multi colored inspirations. Here are I few I thought were interesting.

I think your home is pretty eye-popping now, I would definitely be slowing my stroll to get a better look, but I can understand wanting a cheerier color if your environs tend to be pretty grey. The current color scheme does seem to suit the surroundings. Is there a color you are leaning towards? Would you want the whole house to be the same color or have color-blocking as you currently do? Are the windows to be painted? What colors are "cheery" to you? When I first saw your house a forest green came to mind.

I guess I didn't say that I am trying to deemphasize the brick. Not sure if you can tell from the photo but they are Roman style bricks, lacking the interesting dark colors and white stain of more traditional flat brick. It seems like blues and greys would make those bright pink and orange tones pop. My original thinking was white with dark accents. But I do like the dark exterior colors that are popular now. I worry that the dark colors will just make the bright pink/orange really stand out. Ultimately I guess I am looking for the house to look fresh without changing the good bones that it has. I am trying to embrace the look of the brick. Someone want to talk about how to tone down the brick without painting it?