Did they place a water and ice shield barrier on the edge of the roof to three feet past the wall line? Your roof is not similar, only the material is. Original roof was solid from eave to ridge so any ice formed would just keep backing up the roof without penetrating. New roof is pieces which allow the ice to form and move underneath and then leak in the house.

Existing conditions are that there is no overhang. Not sure how else to describe it. None, nada. Roof stops at the top of the sides of the house. None of the houses in our old neighborhood have overhangs except in one case where the homeowner had it added. It doesn't extend out that much, 1 foot at most, but probably a little less. The roof is 17 years old and does need to be replaced. We just don't know whether we should add the task of adding an overhang to the job. Our climate is almost tropical here in Houston, TX. No snow but a lot of heat. The roofer "does do overhangs", at least according to what he says. Though this roofer was highly rated, we are going to at least interview another roofer. "require a canopy" means (I thought) require extra build out beneath the overhang (other than the standard extension of the studs that are part of the roof) in order to support the overhang. (Kind of like requiring the brackets under each shelf that are used when building a book shelf.) Don't want to have to add brackets underneath the overhang, I don't think.

There are many shades of black and charcoal, I would try some darker grays to find the perfect color for your shutters. The portico color / door color in the photoshop looks khaki, is that close to your mortar color? If so, you might try soft brown shutters with it. Tall narrow trees/ shrubs for vertical lines between the windows is a sort of dated Italianate look that might not be appropriate for your house or location. Homewood is a great area, I love the Tudor style downtown shopping, that is where I had my first lunch at Zoe's. Great schools, too, which makes your home an even better investment. I like the portico your son mocked up! You might also google pictures of a portico style that projects outward (right angle) from the house instead of upward.......like these A pic of same house from farther back:

Who designed the addition? Architect? Was the standing seam roof "layout" included in the plans? If yes...take this issue right back to the architect for correction. All roofs require proper planning for water handling. Yes, guttering is possible on your roof. It will have to be custom made, over-sized, and the leader head & downspout will be huge. Take action now before the Spring rains start.