I think the advice to live with it before doing anything is generally a good idea. That said if it is something I find I can't stand the look of that opinion rarely changes for me and would be a reason for me to remove it. I find it an eyesore and no matter the function I couldn't handle seeing that thing every day I came home and I'm generally a function over form when making choices in design. However those choices still consider how something will look. For the house I don't know how much you want to spend, but I'm going to throw ideas out for someone who has a nice budget. If you want more of a modern look I'd replace both the garage door and front door to something with a more modern look. I'd remove the shutters and I'd also consider putting in new and taller windows on the gable end - this assumes that is feasible in the interior rooms as well. Removing bricks to enlarge windows is something that can be done more easily than the other way around. I'd also work on changing the landscaping to a more modern look

Hi, those are some "interesting" colour and decor choices for sure. I like the idea of grey/white that you are planning and I think a dark colour would look great with those choices. One of my favourites is Benjamin Moore Wrought Iron. It is what I would call a soft black......more grey than black. Here are some photos of Wrought Iron used on exteriors: For trim and or contrast colours, these are the recommended coordinating colours from the BM site: I'd be tempted to find a cream that is a little less beige than this one - something closer to the trim colour in the photo above with the dark garage doors. Once you have your shingle colour you can decide about the colour of the chimney. You could go with the wrought iron colour on the chimney or you could choose a paint colour to match the shingle colour so it would disappear a bit into the roof. There are some folks who are on Houzz that are very good at photoshop and amending photos to show various colour choices.. Alternatively both BM and SW have paint visualizer tools so you can upload your pictures and play with colours until you find a look that pleases you.

If you would like to avoid dealing with any peeling paint in the future, consider staining the wood instead. There are transparent, semi opaque and opaque stains to choose from and they will not peel if applied according to instructions. Superdeck is often sold at ACE Hardware and it's a much better stain than what is available at the big box stores.

First, I'd get rid of the pile of things on the right and the things cluttering the front porch. Don't know what is on the left. A shrub? Then I'd kill the weeds in the driveway. What is growing just to the left of the driveway? I'd also consider painting the white parts of the house in a color that blends with the brick tones.