Well, I would have to agree that if you are moving in two years, you don't want to spend a lot of time or energy on a lot of landscaping. The new owner may not like what you did, and end up ripping it all out and starting over to suit their own taste. That said, I think I'd like to see a small ornamental tree in the area about halfway between the lamp post and house to break up and disguise that large expanse of brick and change of siding material to the left of the big window. Maybe Amelanchier, something not too dense. I'd also like to see something softening the edge of the retaining wall. Low growing Cotoneaster has interesting branch patterns and colorful berries in the fall and winter. Microbiota could cover that bank and provide year round color, or one of the low growing Junipers or other evergreens. That bank is your biggest problem, IMO. Rhododendrons and Azaleas are nice, but once they finish blooming in spring, they will just be foliage. Adding in an Oakleaf Hydrangea for summer flowers and fall color might be nice off to the right side. Unless you go with a Meyer Lilac or a mildew resistant cultivar, you may end up with a mass of powdery mildew for the rest of the summer. Not very attractive. Making the planting area near the house a little deeper to leave some space for a couple of clumps of perennials that bloom at different times of the season will give you some extra interest. Add them in masses, not just one or two, so that when they bloom, you actually can see them.

Match the color of the siding to the red brick. Use white trim and dark blue or dark green shutters. Or paint the siding sage green with black shutters. Not all shutters have to be the "right size". Some houses were designed to have narrow shutters as a colorful accent, not to pretend anyone will shut them in a nor'easter.

I like the last mock up except the windows should all be the same , I have never tried painting roof shingles but does not sound like a good idea.. Good plan to remove the bays and those awnings. If the awnings were actually controlling the light and heat from the sun just use soal dhades inside to do the same thing. Please do not paint the brick

@Indecisiveness, sorry if unclear. First pic are color samples described in the message.