I hate stain. (don't tell anyone I said that) If Cabot is a product option for you, that's a good thing. Lowe's sells sample pots - at least all the Lowe's I know of sell sample pots of Cabot's stain colors. You can mix stain colors easier than you can mix paint colors. The trick is to keep the ratios even if at all possible. Painter may have a stroke if you end up with a custom mixed stain color. That's okay, he'll survive. Just remind him that that's what those five gallon buckets are for. Buy samples. Test colors. Hopefully one straight out of the can will work for you 'cuz that would definitely be the eaiser option. If you have the option of Sherwin Williams, their WoodScapes (solid or semi-transparent) is another really good exterior stain choice IMO. Many colors to choose from, varies a lil from the BenM solid stain palette. Good luck! :D Here is a link that might be useful: Cabot Solid Stain Sample Colors

Have you seen Elizpiz's kitchen? It might give you some inspiration on what to paint and what to stain. There's something about your elevations that make me think of her beautiful kitchen. Here is a link that might be useful: Elizpiz's finished kitchen GW reveal

That's a realtor picture, so the paint doesn't look anywhere near that good in actuality. It probably hasn't been painted in 20-30 years, and it badly needs updating because it looks really old. I want something to pop when potential renters drive by, but I don't even know how to look for houses that have brick patterns like this for ideas.

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.