Your front door requires some protection from the elements.

Even a canvas awning would help.

what good are shutters when they can only fit on two windows?

Nice idea with overhanging above front door from Bev.

Some visual with shutters and landscape

IMO if you are going for thick window trim in the future you do not need any shutters.

I like the idea of some protection over the door and bigger trim. No to the shutters. How about a bigger coach light too.

It seems as if every other exterior dilemma has to do with shutters. And there's such a hate for shutters on this site. I think Celery's visual with shutters looks very nice. The only problem for me is the bright white trim. Can you paint it?

No shutters since only the bottom windows can have tehm and I totally agree you need some kind of protection for guests and actually your front door. Just wait and add the trim and new windows when you can afford it . Add nice planters larger than what you have and maybe corten steel fill them with seasonal plants even things like Christams lights and ceadr for winter /

Am going to go in the "no' shutters group especially if you are considering decorative, non-functional shutters. Will agree with other poster that it would be a good idea to have some sort of roof over your door. Might even suggest a small portico with columns to relieve the flatness of your fascade.

I love @housegal200’s idea. Brighten up,the trim, and also get some kind of covering for the door. A painted door will be very welcoming.

Landscaping can make a huge difference. I would forgo the window boxes and make sure to put tall growing bushes and/or flowers in the middle area.

Rose of Sharon can grow really well. I had one that almost went to the gutters. And it’s a colorful, beautiful flower.

No to shutters, as the won't fit on the upper windows, giving you a half-shuttered, half-no-shutter look. Window boxes are hard to keep looking nice. I would never have window boxes when I could put in foundation shrubs. I have a lot of garden and spend hours every week weeding, planting, pruning, etc. So, if window boxes weren't so hard to keep looking nice, I'd have some.

Fill up your gravel or mulch pit with flowering plants and you'll have plenty of charm. If you use the stone path, put in a series of low-growing flowering plants. I don't know where you are, but moss phlox looks good and is pretty close to evergreen (too much cold, dry wind in the winter can dry it, but it comes back). Heaths and heathers are good, too. Salvias, mini iris, veronicas, etc. That said, you can put some flowering evergreen shrubs in the back.

Portico cedar shake houses--small version of some of these could provide weather protection and interest over the front door. Note that trim matches roof trim.

I found this exterior that reminds me yours. May be you can get some ideas

https://www.gardenweb.com/discussions/6381786/landscaping-help

Not sure if you can fit wide trim and shutters on the top windows. If you are going to change the windows and do wider trim, I would do that first before shutters and window boxes.

Here are some nice pics:

I love window boxes but your windows seem a bit narrow. Get some beautiful plants in the beds and maybe something tall between the windows to fill or a trellis.

I would advise against window boxes under casements that open out. The windows will interfere with any plantings in the boxes.