Keep the shakes! They lend your house character and texture and are fitting for the style. I think it would be bland without them. However, that doesn't necessarily mean you need to keep them stained. Paint is always an option. White is always a classic choice and never goes out of style, whether you keep the shingles stained or not. Greys have been around for some time now and may begin to look dated sooner than you'd like. One idea that I have been loving a LOT is to go darker. Just an idea! Best of luck!

I can see why you'd want to make the bedroom bigger! I would suggest that you remove or move any interior walls before you start painting, so you don't end up removing some later. The flooring looks very nice and will blend with anything. Do you have a source for more of the wooden/wood look flooring so that as you move walls, you will be able to fill in the gaps where the walls stood? By any chance, do you have a floor plan that shows the layout - where walls are and which room is which? Like this - This first link is to an article I found on what the colors trends in the USA are for 2020 - https://www.2020spaces.com/blog-2020-color-trends-interior-design/ And this one is to a blog you may have heard of that is much closer to you - https://www.thenordroom.com/blog I'm sure that others will chime in and try to help!

So the kitchen could fairly easily have some faux beams like the inspo picture of the kitchen I posted. I would put another faux beam across the end of your kitchen to further accent the look in the kitchen. For the living room, could be a little more complicated due to the space and to really get the look you want but can be simplified to faux beams but not sure if that would be in what you like. So I will post the simple and more complex options. any of the more complex ones should include an architect and specialist in your area that can do the install.

I would not do warm colors on this house. you have a very cool blue/gray silver roof. and the house is more contempary. You picture is very small and it's hard to photoshop anything, but here's a more streamlined darker garage door w/windows, and your door is painted a charcoal. for the body you could try one of the cool, slvery blue tones. wrought iron for the doors.