DIY or hiring out? Do you have an architect involved? Budget? You show corner "columns" or extended sidewalls but are you allowed to do them with the setback requirements as you appear fairly close to the road as it is. Why would you want a terrace with an expensive railing on the street side of the home?

What might be really interesting is to put several movable laser-cut screens on the upper floor, that could be rolled on tracks to various positions as the light changed during the day. (although you would need to include horizontal safety rails in the design).

For the lower part of the house, do steeply terraced gardening instead of a lawn. I don’t think a super wide concrete staircase is all that atttractive or safe if it rains or snows If you would like something more user friendly, consider zig-zagging the steps. Another fun idea would be to create a long S-squiggle of big round stepping stones that meander from door to street, with organic plantings along the way, but include a narrow straight up staircase next to it for those in a hurry.

Two comments: First, the digging disruption of the root zone for the trees may cause serious problems. Bring in an arborist to see what can be done at this point. Second, if you want major changes, hire an architect who will come up with a new design for the house that has good proportions instead of trying to find a few piecemeal changes that will look more modern.

What are you doing with the landscaping? The two trees are a beautiful frame for your house and I think the house is unique and charming as it is.

Yes, I hope you are not thinking of cutting down the trees to make your house look ”modern”. You’ll just make it look like you are stuck in the past.

This is where we are so far

Yes, you definitely need a railing. Anyone with bad knees will decline to visit you.

Get rid if that bay window for sure.

I would probably do something with the entrance. Make it look grand. Create illusions. Not sure of ur budget..

Am digging the new stair! The front door - not so much, unfortunately. The slats of the door make it look more like a louver or a prison gate (no offense intended). I would like the door more if there were fewer slats and more glass. Would suggest painting the brick to give the house a more unified look. I do like your bow window on the left but once again there seem to be too many horizontal mullions. They are distracting and would somewhat obscure the view to the outside. Would suggest a narrow profile railing for your upstairs and would suggest repeating the same on your new stair. It's a handsome house. Good luck!

Also get bigger light fixtures. I would add the railing above, it looks like one belongs there. Are those paint samples at the front door?

As have been said already, black colored windows, also replace the bowed window with a flat one. Paint the brick to match the other color using specially formulated paint for brick. On the sides replace the traditional looking molding frames under the windows with something more modern looking, maybe wood like you asked about. Maybe a glass panel railing. Then use landscaping and something on the balcony to remove the randomly placed windows look.