well, 1950's is mid-century, so I think you're on the right track! :)

I'd start by deciding how you feel about the brick/stone -- if you like it, you might pick a lighter greige color from that to paint the rest; if you hate it, I suppose you might paint stucco and stone the same color, any color you'd like. (also keep in mind the roof color and how soon it might need replacing.)

What do you guys think about the wavy facia boards across the top (also on the sides of the house)? I was thinking of replacing them with straight lined hardy plank to simplify the lines of the house.

Landscaping as is works for this year -- unless you're moving the front hedges beneath the wndows. You could see how they "winter" and plan any landscaping changes for next spring. (Shrubs need trimming Would keep those beside the house at/below window sill level. Would likely want to keep a shrub ... create a hedge ... between front yard and driveway if possible. If you move the hedges from beneath the windows of the front of the home this fall/winter, try to reuse them as a border around the property boundary or between front hard and driveway.

Would definitely replace the wavy siding as a part of a redo of that gable roof.

If you're interested in removing/moving the front hedges, do consider creating a dual forward facing gable over a porch that also extends forward and all across the front of that right forward facing gable.

https://www.pinterest.com/pin/171207223323072726/

I think that they are quirky and part of the charm. I would keep them.

Would remove the waves.

If you want a more modern home, you could change the roof over the front stoop/porch to be a portico and have the roof to the right of it extended beyond its current ridge to meet the side of the taller portico roof.

If you want a more traditional/conventional home, extend the current right forward facing gable about eight more feet to add a porch all the way across the front of the home.

I would lean into the cuteness of the house, and not try to make it more modern. I think the more you accept your (really sweet) house as the traditional house it is, the easier any alterations will flow. I would NOT get rid of those quirky wavy shingles! In fact, I would replace the lattice section above the garage doors with a piece of trim that echoes those same waves. I'm not a huge fan of aqua blue houses but yours makes me smile. I have regretted every change I have tried to make to my split level 1960's house that doesn't respect its origins. I've found a lot of good inspiration looking at remodels of houses in Australia and Scandinavia - places where real estate is way too expensive to justify scrapping much of anything.