I agree about prioritizing a new roof - the existing one is quite tired and kind of drags the house down, as well as being a potential leak hazard which can cause significant interior damage. (With snow loads like those, you need a roof rake to avoid ice-damming and leaks!) If you can't afford to totally redo the front steps (after paying for a roof LOL), patch up the chipped-off chunk and paint with textured concrete-patio paint. Not a really long-term solution, especially if you have to use salt for ice removal, but it'll get you by for a while. Love the idea of veneering the steps with natural stone or porcelain (a slate look would be very nice with the brick, especially if it has some brick-colored streaks in it) when you can afford to do so, especially if the existing brick walkway were to be removed and continued with the material used on the steps. Paint the front door a dark green or darkish, slightly grayed blue to contrast with the brick, perhaps with a taupe/beige trim around the window. Maybe taupe/beige for the screen door. Replace the worn hardware with a slightly antiqued brass like Emtek's French Antique. The mailbox and light fixture definitely have to go. Although your house isn't a bungalow, look at some of the Craftsman-style lighting out there because you can mimic the low roofline of the house - repeating elements makes a more cohesive look. I'd suggest a slightly antiqued brass like Rejuvenation's Brushed Brass - their Lowell/Williams (two sizes of the same light) and McKenzie are good ones to look at. Yes, they're rather expensive, but the quality is amazing. Especially in harsh climates, cheap lighting looks cheap and cheesy fast. The "Welcome" sign on the door is a little too cutesy and country-style for the house and blocks the window. Get a welcome mat instead, if you must express the sentiment in print rather than attitude. :-) A larger and more interesting set of house numbers to the left of the large window would be more visible from the street. Look at address plaques and try to tie it back into the door color. The railing definitely needs replacing but I'm not 100% certain with what. Where I live any stoop/porch with three steps requires a handrail, check your local building-code compliance department to see if this is the case in your municipality. I'm thinking maybe just something plain but chunkier may work nicely - something like this? Plant evergreens and perennials (as well as annuals if you don't mind the work) around the steps themselves. If you use something low-growing right in front of the (gas?) meter and something taller directly to the right of it, the meter will be disguised but still accessible to the meter reader. I'd also put a planter of flowers or a small evergreen in that dead spot next to the door. An unsolicited longer-term suggestion - when you can, think about repainting the foundation to a slightly darker value of the brick color, or a deep warmish gray. The white foundation makes the house look like it's floating. Also, consider repainting the white trim to something like a camel color, since the white is too contrasty with the brick and accentuates the smallness of the windows on the front of the house. Another repainting thought is to try to match the gutter downspout to the brick color so it isn't as "in your face" - aluminum guttering can be painted easily.

You could put molding in to break the walls between the upper part and lower part. If the upper part is easy-ish to keep clean as white then you could leave that part alone and just paint the lower portion another color (maybe the same green or a light yellow. The molding would make a tidy visual break.

Well I went to BM and got the Aura in a semi-gloss. I think that's the right one to use. I talked to the guy there and explained my project. I also got tinted primer. I will wait for a nice dry sunny day to do the painting. I'll apply the primer and apply one coat the next day and (even though I don't have to wait) apply the last coat on another day after that. First things first though. My masonite to hardieplank replacement project starts next Monday. I will paint my front door when all of that is finished.

Black should cover very well....why would you do 3 coats? Also, what do you mean that the paint 'peels up'? I doubt that this is a curing issue after two weeks. It could very well be that the Martha Stewart paint is just simply garbage paint. Not only that, black is going to be the hardest color to apply on a steel door with any brand if the paint is latex. If you paint in direct sun or on a hot day, this will just make things more difficult. If you have peeling paint on the door now or areas that were pulled off because the paint has already started to set, then simply applying more paint over this probably will not work....black shows everything.