Plant up the yard. In particular, have a pretty flower spill over the wall. You can't do much about the steps. Depending on the geography, you might add a landing pad in the middle of the steps.

Thank you. Would you do shutters on the windows?

No shutters. Professional landscape and hard scape.

Doesn't look like you have the space to do anything about the stairs but I suggest you work on the landscaping...

Thank you. Would you add flower boxes?

No flower boxes. The upkeep is a real PITA.

No shutters , some landscaping , and IMO window boxws might be worth it if you live where plants don't freeze in the winter . Th steps no way to really fix that We lived in a place where the back was pretty flat but the front was crazy steep set of stairs we just had out guests come to the back

Is it a crazy thought to add a front door and small porch? Or add a side porch and keep the side entrance? Sorry pics loaded twice.

I like Property Managements suggestions. Not sure adding such would even be possible as it might put you over building setbacks. Also, adding a porch won't be cheap like adding shutter (which I recommend you don't do) or changing paint colors (which I do recommend you do). Good luck!

Ask your neighbors who they used for cleaning the front garden wall. Have the wall, public sidewalk and your staircase pressure washed. Add professional landscaping- you won't need much. Have the landscapers clean up the dirt and edge neatly around the city tree, but don't mess with the tree itself.

Good quality curtains that don't droop or sag on sturdy rods are essential in making the prominent front windows look good. They should be lined with the customary white lining since this is a traditional house.

Does the house need a new roof?

No the roof is good.

No flower boxes, no shutters, no front porch. Landscaping, paint the foundation a color similar to a cement color and maybe a more tame house color as quite honestly I find that color quite jarring and hideous.

The sky's the limit but maybe not your budget... Perhaps you can add a side porch if you have the space but we cannot see the side of the house at the top or the stairs (something like your 1st picture). I would prefer that look to the one with the front porch.

I suspect you aren't going to be able to put in a porch for any amount of money that would be worth it. You don't have a door on the front and I'd be surprise if you could put anything on the side, because it would be right next to the neighbor's house.

I'm neutral on upper shutters. Hard no to shutters on the lower window. No to flower boxes. I'm an avid gardener and I would never put any in, unless, possibly, I had no other place to plant anything --- but I'd get a community garden before I did flower boxes.

Some thoughts:

Embrace what it is. It's on a hill. At least you'll have excellent drainage/no flooding. Zone appropriate flowers like white roses would look nice there with boxwoods or other low evergreens to give winter interest.