some ideas

In your shoes, I would get a contractor in to pour a larger concrete stoop with steps and widen the walkway from the front door to the sidewalk. Right now it looks like the previous owner just put in a temporary small step(s) to get people in the front door. Take some time to plan the direction you want to go - contemporary or something else. Personally, I prefer those type of windows to not have shutters unless they are sized right and functional looking. Also, change out the front door. Your current door is a Victorian type style (oval with 'leaded look' glass). If you go modern, do a modern door. If some other design, do what works with that design.

Here are a couple of different ideas for your front entry, depending upon your style:

Wide stone or other masonry steps as well as wide landings top and bottom

Widen the front walk so two people can walk abreast.

Add a roof over the front door; If you use Doug's lattice type of structure, cover it with transparent roofing so someone standing at the door is out of the weather.

I like the garden placements in Doug's sketch. You may want to include some plants that will have winter color, either evergreens ( broadleafed or conifers) or bright twigs like one of the smaller red-twigged dogwoods. Tie it all together with a single evergreen groundcover and use undyed mulch until it fills in to reduce weeds.

Open, white picket type fence, either wood or powder coated metal as Doug has shown

I am not sure that shutters would be an improvement for this house.

Prune the lower limbs of the left tree so they are not hanging down in front of the lower window, and read up on pruning of fruit trees. They will looking gorgeous for a week in spring!

If budget allows, add a covered front entry to the house. Denita makes a good point about the style of the door. A few inspiration photos:

Oh wow, thank you so much for the advice you guys! I really appreciate it!