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I assume you would hire painters? I'd maybe ask them for suggestions ?

Can you do a few relatively large test squares? We had our house painted gray and I'm so glad for the tests because two of the three were waaaaay off.

We just picked a new house color! If you go on benjamin moores site, you can upload a picture and select areas to "paint" to visualize what it would look like on your house. Then definitely get little test cans and put it up on the house. I was ready to just go for it, but DH convinced me to do a test patch and thank goodness we did! It looked soooo different. We ended up testing 4 colors before finally finding the perfect one and love it.

Are you going to paint bricks? I'm not sure I would choose painting it because the upkeep is so much higher on paint.

Eta I think you are saying paint other parts in a color that compliments the bricks, but I'm not totally sure.

We just painted the exterior of our home and it was so difficult to choose the colors! We had to pick 3 colors: body, trim and front door. Unlike you, we matched the garage door to the trim (white) instead of to the front door (red).

Here's what I did:
1. I grabbed a bunch of paper swatches from Sherwin Williams and looked at them in natural light. You could tape up the swatches next to the brick to get a feel for what it will look like.

2. DH & I picked a few of the swatches to get samples of ($7 each sample... gets expensive if you get too many, but the wrong color is a much more expensive mistake!) We got 4 different grays with slightly different undertones: true gray, blueish, purpleish, brownish.

3. We painted big swatches on the house in several areas. We were painting the ENTIRE house, so I wanted to make sure it would look good in both shade and light. Paint 2 coats and don't make any judgments until it is dry! The color we ultimately chose looked awful when it was wet! It looked so much better after 2 coats.

4. Ask Instagram friends what color we should pick

5. Stare at colors at different times of the day and from afar as well as up close.

We also crossed our fingers and toes that we didn't pick the wrong color and thank goodness it looked amazing when it was done!

I don't think our painters had to do anything special to cover the areas that we had put samples on.

ETA: Oh I forgot to mention -- if the paint is already chipping, you might actually want to sand it down so it is smooth when you are repainting. You'll also need to clean the surfaces (and let them dry out) before painting. I read on a bunch of websites & heard from painters that prepping is a big component and makes a big difference in the quality of how long the paint job will last.

For color selections, I like the curated ones by Sherwin Williams. They have colors that work together so you take all the guess work out of the doors, trim, siding, shutters, etc.

If it's chipping pretty badly, a pressure washer might be a worthwhile investment also to get the paint off. So much easier than scraping, (you still have to scrape, but not as much) and it cleans the old paint surface too. We didn't use TSP, I think that's more necessary for kitchen surfaces where it's greasy and all. When we talked to Sherwin Williams, they recommended an oil based primer on any bare wood and a latex paint on top. And SW has 40% off paint sale all the time (even on their little regularly $7 test cans) and you can just buy the paint in white during the same, then bring it back whenever you want to tint it.

@PurplePumps: we did Functional Gray. SW 7024 I believe. I'll come back later to post a pic!

@sunny: That's pretty close to what we did! We ended up using Warm Stone SW7032. We tried one shade lighter, Mega Greige which look so perfect on the swatch, but looked shockingly light once we put it next to our trim and wanted more contrast so we moved up to the Warm Stone which I would have sworn from the swatch would be too dark. Paint is so darn tricky!