I actually don't mind painting brick, though I strongly prefer staining brick but so long as you use the correct product I actually like the look of painted brick. You must use a vapor permeable paint, and painting increases the maintenance required for brick considerably, but if the look is completely outdated or inappropriate to begin with then sometimes painting brick can really update the look. Having said that I live in the land of red brick houses and they bricked everything even craftsman influenced houses where brick is not appropriate at all. However, I think painting the brick is the least of your problems. If I owned your home I would start by planting a nice tall cypress (or anything tall and thin) along the left edge that distract from that wide brick border on that side. I would then cover up the lower brick border with some sort of hedge or bushes that break up that line between the brick and the siding. If I had the budget for it, I would remove the vinyl siding and either go with a darker grey (or a blending color) wide board hardie type siding or staining the brick into something softer. Before you take my advice, this isn't something that I excel at personally so other posters might be giving you better advice than I am. The other and probably best option is to remove some of the brick, add brick in other areas and then paint or stain the whole thing to update the look, however, that is a significant expense to accomplish what a great landscaper can do for 1/5th of the price.

post photos if you can

Personally I'm a huge fan of painted brick. I lived in a house that was painted Charcoal grey with bright white trim. One of my absolute favorite looks is brick painted white with black trim.....classy and timeless. I would paint everything, don't go with a natural color (like trying to match the stone) , go with the color you want your house. Yes, agreed it is permanent, even repainting another coat or color is a bad idea. One painting (meaning primer and two coats of your color choice) of paint on brick still allows the stone to show texture. If you start layering that up it looks cheap. Unless you have experience painting, you must hire a professional.

You need a special paint for brick if you paint it. Regular paint, will cause the brick not to be able to breathe, and yes, it can cause a lot of damage. I would prefer a wash, rather than a solid paint, since to me solid painted brick, looks a bit like plastic.. This is one brand of paint, that you could use. Please do a search for all the info on it. romabio. Myself, unless you have really ugly brick, I wouldnt paint it.