Budget and building codes permitting, you could recreate your entry. You might ... Remove the first floor roof from above the front stoop -- everything from the brick to the garage. Create a new forward facing gable roof over that area beginning at the ridge of the upstairs -- at least at that height or even above it -- and extending the roof of that forward facing gable to a point at least twelve feet in front of the downstairs exterior wall. About six feet of this will be your new front entry foyer with your front door moved to the new exterior wall facing the road. The rest will be your new front porch. Alternately, you could extend the forward facing gable roof only six or eight feet beyond the front exterior of your home to create your new entry foyer and then add a shed roof with two hip corners for your new front porch. You'll be enlarging the upstairs room on the left by extending the floor of that upstairs room into the vaulted ceiling space above your new porch; then you can move the original window to that new upstairs exterior wall of your forward facing gable. What front door and front porch post style you use will help define/redefine you home. You could also add an arbor across your garage that coordinates with the posts you use for your new porch.

Lower the dormers to meet the windows and not peak above the roof line - That will be pricey but worth it and a lot less expensive than removing the gambrel roof. Paint the brick with a masonry paint or lime paint. Don't do a wash that exposes the brick. The house and roof together are both busy, you need to tame one of them down and it's cheaper to tame down the brick. I know folks love to recommend a wash that shows some brick, but someone did that in my neighborhood and in person, it looks awful. Can't quite see the lower windows, but they look like they need to be freshened up. Are those storm windows? Storm windows do the job but IMO, cause too much reflection as a single plane if you're going for cottage. You need the mullions to break it up. Get good quality windows in a style you like. Black shutters Make your front door more prominent by removing the storm door. If you need better energy efficient door, get that and don't replace the storm door. If you need the storm door, get a good quality one with low profile styles so the door will show. Paint the siding the same color as the brick New handrail that compliments the overall look. Not sure what that is but once everything else is done, you'll figure it out. Landscaping. If you really want to use or maybe exceed your budget, do cedar shakes on the gambrel and roof. My neighbor has a very similar house and did cedar shake on the front of the gambrel and the front of the roof. They did asphalt shingles on the back to save money. Looks really nice. $50 - 60K seems like a lot but it will go fast once you start making changes that cut into the roof line. Plus good quality windows are crazy expensive now. Make a plan, price it out and you can make your lovely home spectacular on that budget.

Interesting - I like your theory about someone homesick for New Orleans LOL. As mentioned above, porch cant really be removed without leaving scars - and an overhang much deeper than the rest of the house, which would look funny. Can the balcony be used, does it make sense to open up a room to it? Part of its oddness is that its obvious that there is no door and cant be used. Whats going on under the porch, behind the hedge? Some kind of patio? You could remove the hedge, expand that and make it into useable attractive outdoor living space - framed in a border of flowering fragrant shrubs, 1 or 2 well placed ornamental trees (ie short, placed toward the side of the house), intermixed with perennials/bulbs. You could leave a few of the evergreens - its just the solid wall of them that is so unappealing. What are the rooms on the lower level - would any of those benefit by opening up to a patio? .... or maybe it could be an actual courtyard and by that I mean a professionally designed walled space which fits architecturally with your house.... not an ugly cheap privacy fence from Menards! But then that gets to be expensive too - probably more than just removing the darn thing! Otherwise, maybe just swap out the frilly iron work for something simpler/more linear, with strong horizontal lines as is fitting for this style/era. Also changing all the white to something less high contrast - would help de-emphasize it.

There's a strict school of thought that shutters should only be used on window styles that would historically have had shutters that actually open and close. And that any non-operating shutters should still be wide enough that they would close if they could. My view is that shutters can be a purely decorative element, free from these rules, and still look good. So I would leave your shutters, because your upper windows are relatively small compared to the size of the space they are in, and the shutters make them look more proportional to the space. I think they're just the right size. So then I'd also leave the shutters on the windows below them. I'd remove the shutters on the larger window on the porch. Whatever siding colour you choose, I'd go with a medium tone - neither a very dark colour that could look overwhelming, nor a very light one that would pop out. Use the same colour to "paint out" the contrasting belly band between brick and siding, and also paint out the corner edge pieces on the siding (can't remember what they are called). Your front door is beautiful and perfect with your brick. Congratulations on your lovely home.