The flat trim board under your windows will cause leaks if it was not flashed properly or if the sill nosing doesn't project and overhang enough for an effective drip (in the traditional manner). Sealant/caulk at that joint is only temporary. I've seen this detail cost owners a lot of money so make sure your contractor knows what he's doing. One solution is to add a projecting PVC sill nosing in place of the flat trim. It's difficult to beat the traditional double-hung window sill design. Here is a link that might be useful: ATW

I agree do a dark color on your trim. I would do a light color on your siding. Is Benjamin Moore available by you? These are colors I can see on your house.

@tfitz1006 There were flowers around the fountain and in large pots on either side of the front door just prior to painting. A purple passiflora vine normally grows across the garage - all of which will be replaced, don’t worry. There is plenty of color in the back yard which receives full sun. But the beds on either side of the entryway exist in shade 90% of the day. They are also limited in size due to necessary driveway access to the garage door. I’m happy with the mid tone green gardenia with white flowers and the contrast of dark green dwarf ilex and ligustrum in those beds. If I took a picture from the street you would not see the house in full. What you don’t see in the front is Yesterday Today Tomorrow as well as a silver bismarck palm to camouflage the garage. Starburst Clerodendren on the side of the garage has fuzzy leaves that are dark green on top and purple underneath with pink blooms in the winter. Violet pentas surround the three other palm trees in the very front and the mail box. I grow orchids in the live oaks on either side of the driveway at the street. There is always something blooming but not all at once. What you also can’t see is a citrus garden on one side of the house and a butterfly/hummingbird garden on the other but I won’t bore you with everything in that. Suffice it to say there is plenty of visual interest and curb appeal, in keeping with the Mediterranean style which is less about color and more about texture. It was an intentional decision to keep the front of the house a bit more formal and less busy in color than the back and sides. Actually I’m kind of known for my gardening and if anything I have a lot going on in the front. It is definitely not boring, especially compared to the low maintenance yards in our neighborhood here in Zone 10. :)

Remove the shutters entirely, get a larger lantern light (1/3 of the front door's height) and then decide about the paint. Depends on your neighborhood, but I think a light charcoal gray or a sage green might be pretty. What color is your roof? White may be too "safe" but that depends on the demographic of potential buyers.