IIRC this is the house reno purchased to renovate and sell, so it just doesn't make sense (as lisa mentioned above) to dump a lot more $ into cosmetics that in all likelihood a buyer is going to change anyway. (But then reno knows this from experience, don't ya? ;D ). Honestly, looking at it from a buyer's perspective, it looks presentable to me. (Although I do like it with shutters back on and more neutral garage door.) If a paint tweak makes you more comfortable, then I say go for it , it's a quick cheap fix. BTW, I was showing DH your house (because I've been bugging him to get into renovating, it's something we can do ourselves. My father enjoyed Real Estate dealing as a hobby and did very well for himself rehabbing homes on the side when he was younger). DH wants to know if the driveway is the kind where the gravel soaks up and disperses the water below ground? (I have no idea what he's talking about, don't see those around here, but he does, so hope I phrased it properly! ;D )

Taking the siding to the ground might not be the best idea, My husband put a coating on ours (think it was called Fibercrete) that made it look more like poured concrete that block. Then we just left it the concrete color. If your ambitious and in a cold climate, it is possible to add rigid foam insulation the the exterior of the block... https://www.familyhandyman.com/walls/foundation-insulation-panels/view-all/

As I despise black trim my suggestion is monochromatic. Paint all trim, siding and the bay window area including garage door. and front door sidelight the light gray (middle one of your 3 samples). Paint the door and shutters and very dark charcoal gray. Your house does not need to be outlined in black. Then the landscaping needs to be improved

Do not paint brick. It is likely to cause damage to the brick over time, and painting has to be redone about every 10 years. Your brick is a nice neutral color. However, if you must color it, use a paint made for brick like this ONE with a 20 year warranty. Here are some of the colors offered by this company. I would get rid of the shutters. Your windows are too wide, so shutters don't make sense. Instead, paint the trim around them to make them pop. If you can replace the trim with wider trim all the better. You can also paint the fascia and the vertical corner trim to add contrast. You can paint the door black as well, or choose a separate stand out color for the front door. Here are some photos of homes with contrasting trim. Link 1, Link 2, Link 3.