I think that some fairly inexpensive things could make a dramatic difference. First I would replace the iron columns with some more substantial 6x6 supports (with some moldings perhaps) and add some railings. Also, I would not paint the porch, but stain it. I think taking out the concrete porch would be a very big project. I would also add railings and wider wooden steps to the front door. Paint or replace the front door for pop and in your individual taste. The shutters look out of place and out of scale for the picture window. Shutters should look as if they would actually work, these do not. Once this is done the right of your house would be heavy and you would need to balance this out with a nice curved bed on the left with a fairly large tree to add balance. Zone 5 maybe a nice magnolia. Fill in the large bed around the tree with some nice plantings. Towards the road cries out for a small fence with a gate or maybe some hedges with more beds. A flagstone path up to the front steps. A small tree (maybe a Japanese maple) on the right and curved beds along the walkway and driveway. I think this would take your home from plain to fantastic with the least cost and with things that you can probably do on your own. I am sure you can. I do like the idea of shutters, but think you should look at different sizes and styles. I don't like being critical, however I think that by asking for help you are probably looking for honest evaluation.

A pergola is lovely in a place with lots and lots of sun. Elsewhere, it can get dark and dank in the winter. I'd make a path to your door. Much of it can be part of your driveway. Just replace with brick or pavers or something visual that you can still drive on. Then, I'd clear out the shrubs along the side of the house with the door. I'd turn the bed by the right front of the house into a semi-circle no larger than the width of the house and have a variety of plants and heights instead of that yew hedge. (Not sure it's yew, but it looks like it). Window boxes are hard to keep looking nice. They don't have a huge amount of space for roots, keeping them watered enough but not soggy can be a challenge. This is why you see a lot more window boxes in carefully staged Houzz photos than in real life.

Your home is darling! I think your efforts and budget are better spent toward a cottage landscape and some dark blue-gray shutters. The cost of removing the dutch colonial roof (adorable, BTW) and adding fake dormers is not worth any perceived benefit you may have. Note that the roof ridge height is consistent across your inspiration house. Our last house was a trilevel which we spent a lot of money renovating and ultimately moved because you just can't renovate the split level out of a split level. Unfortunately, the ROI in a split level in my area is frustratingly low. Keep that in mind as you do things to your home.

Shutters should appear to be operable, so they would need to be as wide as the window... so if closed, they would cover the window. So no shutters on your house. I agree with taking out the boxwood that have been butchered. If you take the bed all the way to the sidewalk, you need a pocket bed on the left side. Yes to learn more about pruning the Crepe Myrtle. Ever heard of Crepe Murder? It's a thing. LOL Honestly you don't even have to prune them. We had several over 30ft tall at our last house, but you don't want one too tall right next to the house. Having lived in the South all my life, I don't have a problem with the grass since we get rain. No idea where you live, but the grass looks healthy. Unless you want to spend every weekend gardening, or hire a gardener, I would not go to the extreme of removing the grass. If there room for a wooden bench on the front porch?