Instead of painting the brick, if you still don't like them after having them sand blasted, consider staining them rather than painting them -- that would be a mistake. Seriously consider extending the deck the full width of the house -- better for use and resale value. alternately, build a covered porch from the deck and wrapping around the corner of the house, stopping at the chimney. If the deck (or a porch) were extended all the way to the end of the house, the higher ground would mean you'd only need a couple of steps to reach a patio on the end of your home. justgottabeme has the right idea with painting the foundation and window frames and siding already painted; however, you might consider using CWF or a dark, absorbant stain on the deck top and rails, painting only the posts (even with the foundation) rather than painting the actual deck or using a "solid stain" that looks like paint and, in my experience, doesn't hold up all that well..

Your home is very nice but the problem you're having deciding what route to go is that your home is a mishmash of different styles. The roof screams coastal south yet the brick yells colonial. Add the shutters (colonial) and the Roman pillars (colonial) and it amounts to a split personality. The first thing I would suggest is getting rid of the fake shutters. Unless shutters actually have a purpose it's better to ditch them. The columns are a little more problematic because to change them will incur significant costs. I would go with a simple square column for their chameleon-like properties. But make sure the dimensions work in relations to the size of the home. As much as I am an avid gardener I agree that the shrubbery at the house perimeter needs to go. It overwhelms the home and makes it appear much more squat than it actually is. I don't have a problem with the other greenery, though. I have no experience painting brick in such an environment. Bricks helps release humidity in a building. In Canada where I live, painting brick can be problematic. The continual effect of moisture trapped in the brick can deteriorate it over time. While I live in the north I have a place in south Florida. Most painted homes I see are stucco which lends itself to paint. Paint would be an easy and cheaper fix in the short term, but I believe it would require constant attention and over time the costs could multiply. I think your dissatisfaction in your home's appearance is less because of the brickwork but because of the stark contrast of a very light roof against dark facade. Try painting your front door a different color (the red just accentuates the colonial vibe) that works with the brick and the roof before making the leap to painting the whole house. I suggest SW's Sea Serpent. Paint the columns (not the door color) as well but a muted shade like SW's White Flour to get an idea of what your home could look like without going all in on the facade. I noticed you used an app for a combo of house paint and shutter colors complimented with blue and white greenery. As an expert gardener, I have to say my experience with blue and white florals paired with rich dark greenery , which are absolutely sensational, really only work in environments that enjoy a lot of shade. It's the shade aspect of the colorations that makes the pairings so luminous. In a sun drenched environment like south Florida they look washed out. My final suggestion if cost is not an issue would be to hire someone, after investigating the effect of paint on brick, to stucco your home's exterior. No better time after pulling out the foundation plantings.

Like the pergola over the garage door idea. If built to be sturdy enough to walk on it, then it could serve as a fire escape route should the need ever arise -- certainly hope it never does. You might also consider painting your step rails and side supports the same color as your siding unless you're planning to have a wood finish door and/or a rustic porch and post addition over the entry at a later date, in which case you'd want those additions to have the same wood finish. (Might apply to any pergola over the garage as well.) https://www.bing.com/images/search?q=images+rustic+porch+and+post+entry&qpvt=images+rustic+porch+and+post+entry&FORM=IGRE

Thanks again for the input. I tried a color visualizer, but it turns out that I have the artistic ability of a 4 year old on acid. Id love to be able to see some greys or even dark blues and how that would look....(if any of you more creative people have extra time). Thanks again, this community rocks!