IMO work on the actual landscaping first and I always like a walkway from the street to the front door it give a place for plantings and IMO looks a lot nicer than just that walkway from the driveway. BTW your shutters do not belong on those windows so the window boxes could be very nice and replace the shutters . No shutters ever on the door. A new garage door could be a good facelift too

What kind of siding is on your home? Is it in the budget to change that? How many years has it been that color?

It’s vinyl siding. It was painted beige about 7 years ago

Flower boxes are hard to keep looking good. In hot weather, they dry out in 20 seconds flat, there's limited room for root growth and hard to keep looking nice in winter. Most of the pics you see are boxes freshly planted with just purchased plants.

inspiration photos