@HALLETT & Co. The original owner added the brick planter in the late 1980’s and they’re crumbling and safety hazard. I don’t think they offer any curb appeal. Especially the long planter to the right of the door, it seems odd. The smaller one near the garage is ok but not great shape either. The tall brick stacked next to the front door is original to the home, it’s staying put. We found out my husbands best friend’s great uncle had this home built and we have confirmed those aren’t original. I feel better about doing away with them.

Since you are replacing the siding, consider adding thicker trim around the windows as opposed to shutters. I am not sure that board and batten siding will be an improvement. It is a siding that tends to be country to my eye, and your style inside doesn’t convey that at all to me. I would play around with a photo of your house to see how it would look. All the examples shown have some other architectural details that step up the interest such as a porch or dormers, and I think the board and batten may not give you the appeal you anticipate. I like the idea of a more attractive door for the garage. Look at a range of styles; I have seen ones with windows in a column down one side that might suit your home, a single door rather than the two doors in the photo link below. Consider replacing the screen door with a different style. I think a single panel without the dividing line in the middle is a more updated look. Or alternatively, use a roll up screen that pulls across when needed and is out of sight when not. Updated light fixtures will help as well, by the garage, front door, and on the post. The one on the post should be at the end of the walkway, which might benefit from coming down along the drive a bit so that if a car is parked in front of the garage, the walk is still accessible. Once all the exterior fixes are done to the building, then widen the walkway and steps and center the steps on the door, being sure that there is a large landing at both the top and bottom. Remove the pots around the steps now since they are making a narrow space feel smaller. If you want a pot to either side of the steps, plan space for that when you are redoing the steps. I would enlarge the bed around the tree as in Yardvaark's sketch using more of whatever the current plants are if they seem happy. It is difficult to get new plantings established under a maple tree due to root competition, so I wouldn’t plan to change out what is currently there. The beds along the front of the house are currently far too small front to back and so look pinched, and I doubt that anything currently there is worth saving. I would repost about the landscaping when the exterior work on the house and entry path is done. To get good suggestions for landscaping, we need to know where you are generally and your USDA growing zone along with your goals for the yard beyond curb appeal (if any) and how much you enjoy spending time gardening. Some photos of front plantings you find appealing will help as well.

I would need to see the house.

i like the first pic Celery posted. With the panels painted to closely match the brick. A question...do you intend on keeping the blinds closed on the two rooms on the right side? The white of them, compared to the dark glass of the open windows on the left is off. I wonder how your house would look with all the windows (with or without shades) the same basic color. When the window shades are unapplied, i do like how the windows look with the roofing. And i think if you were to go with that slate gray theme a little bit more it could look pretty special. Nice dark green ...even blue-tone shubbery/planting would finish that look.