I completely agree with Annie above, that was pretty much what I was thinking when I read the thread. The cost of a new roof and gutters with cantilevered out overhangs will be in the 20K range, adding the dormers over each front window will be about another 10% and add space upstairs for future remodel. The value of the house as it is should be taken into account before you do anything, though. In neighborhoods with lots of 1940's homes, there sometimes is a shortage of larger homes for growing families and anything you can do to make the home larger and maintain character has a payback on resale.

If you're looking for help with foundation planting, the picture is too fuzzy, from too far away and doesn't include enough space surrounding the house (beyond the side lot lines.) If you don't get the help you're looking for, you might return when you can add some better pictures.

I would get it power washed to start and make any repairs necessary to the steps and aluminum siding. I think you can get away with keeping the brick as is if you put a pretty flowering bush between the two units, something that blocks the massive front wall. Ideally it will keep its leaves all year, or offer something pretty like white berries during the winter. Also, replace the front door of the right unit, and plant something in front of the mismatched brick. Definitely upgrade lighting and put in a stamped concrete walkway - will be less then pavers.

Keep in mind your neighbor so that whatever you do harmonizes with them. We get that you want to put your own stamp on your new house, but it does have its own character and style to take into account. Just forget gray (even though your neighbor has it). Work with your warm palette of dark reds, brown roof, golden grout. That's your palette, not gray and black. --The brick is great. Don't touch it--works with roof, trim, period style. No siding. Work with roof, current taupe-y trim, red brick in a coordinated way instead of trying to remuddle with gray. If/when you need to replace windows, go bronze, not black. Here's the palette to shoot for in trim, pathway, etc. that pulls together red brick, brown roof, and windows. --You need new railing and porch before you think about walkway. Match the style of railing your neighbor has, but paint it a golden taupe. Steps can be taupe with brick trim as in this house below. Are you doing a small porch across the front? Then match porches your neighbors have only in the golden taupr. Front door: taupe as below (note bronze windows) dark red, or teal. Note the large golden stepping stones in photo below. You could do that from the driveway where you get out of the car. The ground in most places is getting soft after winter, so it's a perfect time to lay down stepping stones per YouTube. Plan small garden borders with perennials and low shrubs on each side also as shown below. It's a tiny space but could be a lovely pathway up to your new stairs, door, and house.