This suggestion is a little outside the box, but hopefully will sparks some more ideas for you. In my old neighborhood, there were homes called "side splits" where an entry next to the garage lead to a foyer type situation and you walked up a few steps to the side to enter the main living space. I'm thinking this may be a solution for you, especially living in NY you might appreciate a main entrance that doesn't just dump you right into the living room. An awning above the new front door on the driveway level helps define the entrance.

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 do board and batten on the top same as the side. Stain the brick not paint it. pull out that giant shrub by the garage, extend and wrap the porch around to the side. add the curves into the landscape not the porch. I would first think about what color to stain the brick and then build from there. https://www.houzz.com/discussions/5203840/1960-s-colonial-exterior-remodel-how-would-you-update-this-look https://www.americanbrickstaining.com/2017/08/02/important-differences-painting-staining-brick/

There's a strict school of thought that shutters should only be used on window styles that would historically have had shutters that actually open and close. And that any non-operating shutters should still be wide enough that they would close if they could. My view is that shutters can be a purely decorative element, free from these rules, and still look good. So I would leave your shutters, because your upper windows are relatively small compared to the size of the space they are in, and the shutters make them look more proportional to the space. I think they're just the right size. So then I'd also leave the shutters on the windows below them. I'd remove the shutters on the larger window on the porch. Whatever siding colour you choose, I'd go with a medium tone - neither a very dark colour that could look overwhelming, nor a very light one that would pop out. Use the same colour to "paint out" the contrasting belly band between brick and siding, and also paint out the corner edge pieces on the siding (can't remember what they are called). Your front door is beautiful and perfect with your brick. Congratulations on your lovely home.