Do it right or don't waste your time, especialy since the access is difficult. Tear out the current soffits and remove the underlying restrictive wood. Make sure your attic insulation isn't impacting the air flow and install baffles to make that happen. Then reinstall vented soffit for the whole eave area. However, a vented soffit works in conjunction with a ridge vent for your roof, so that needs to be installed as well. Cutting more holes will NOT help at all. Everything works as a system. Or the alternative is to make the roof the sealed plane and to create an unvented attic. That will take some $$ in spray foam insulation however and is less DIYable because of that.

Very cute house, I like both versions and agree about the shutters, in that I would remove them entirely. Instead of a darker teal door, I might go with something a few shades lighter. If you use the golden yellow, I would also go a couple of shade lighter in that regard too. I think the reason the White Raisin looks good on the sample picture may be because the house is larger. On a smaller home, the bolder yellow may not work as well. I know this isn't an option you were thinking about, however there is a house similar in size to yours not far from where we live and it's the most unexpected color of teal, very similar to this and in person, it is so pretty!

What a charming house! How old is it? It has lots of potential!!! I think that properly sized REAL wooden shutters would look great on the central portion of your home (not on the bay or the window above the bay). I would even go so far as to ornament them with shutter dogs to add character. If you add shutters, I don’t think that adding additional trim around the windows will be necessary as the shutters will frame them. I note that the siding is different on the central portion of the house and the dormer. But painting them all the same color will minimize that difference. You could paint the siding a different color than the brick. But obviously, power wash everything before your begin! A new, recessed light under your entrance ceiling will be less obtrusive. And a pretty bold color on your front door. No need for a portico. But consider widening your sidewalk and pulling it much further forward so that you have a planting bed along the front of the house. And yes to developing a long-term planting plan. In the meanwhile...Plant annuals in classic pots at the entrance to your home. LOVE your home!

Maybe a bigger project that you envision, but I would replace the porch surface with brick, add a broad, deep step off the porch and an equally wide brick walk to the street. Take out the odd little brick bed next to the house and use those bricks for the step, if nothing else. You could also remove all the brick bed areas and use them on the porch.Or you could replace the brick with concrete and face it with your own bricks sawn into 3 pieces to use as facing bricks. Pick up on that orange brick near the step to paint the front doors ochre or sienna. I would paint all the trim, porch siding, column and garage in back with a soft white like those two bricks just below the left corner of the front window. Replace or move your house numbers to the column or to the brick wall opposite it. Other than the azaleas, which I always love, I would replace any non-blooming plants with more azaleas or with low growing evergreen shrubbery that will stay below the windows without you having to maintain it.