I read the instructions on the calk recently or maybe it was the exterior paint - just painted house .. whichever said prime unpainted area's before caulking. Would think you don't want to put it over older paint either as that paint is a poor base too. Primer is made to grip, caulk is made to tugg and stretch and be replaceable.

Paint peeling from paint is not a good thing. It means the undercoat was not clean and dull. But don't worry, the job can be done! The first step is washing the surfaces to be painted. I use Jomax house cleaner. It works for general cleaning or mold and mildew removal with bleach. It's safe for shrubs and plants too. So, wash the surfaces and rinse. Let dry. DO NOT POWERWASH. Read the Jomax label. Buy a good Wooster scraper/wire brush and scrape loose paint from the surfaces and lightly sand the edges of old and new paint with #150 grit sandpaper. Apply one coat of Peel Stop. Peel Stop is made by Zinsser. See the tech bulletin that follows this post. For the finish coat, I would use Sherwin Williams Duration in your choice of color and sheen. Michael Here is a link that might be useful: Peel Stop

Here's the front porch with the new porch light:My brother Kevin bought the red mailbox in Palm Springs the last time we were there - it is difficult to find interesting mailboxes, but I think this one is okay. The porch light is new, and I bought it and installed it temporarily before the painters started because I wanted to get it fitted in first. It is from Kuna, but I bought it at Lowe's, and it was the first one (and only one) I found that has LED lamping and motion detection with a modern design that I found acceptable. It's not the greatest or most interesting design, but I am okay with it, and it is infinitely better than what we had before (see photo way above). This sconce does much more, however, and I have decided that I like the added features. First, it has an additional security camera that only starts recording when someone approaches the door, and it makes a doorbell sound outside as well as on my phone to let me know that someone is at the door. I also see the photo/video of the person on my phone. The other two security camera that we have are hardwired to a screen just inside the door, and these cameras start recording when a moth flies by or when a cat walks on our driveway, and so they are a bit too sensitive, but I think I might be able to adjust that. The old security cameras are not equipped with WiFi (I didn't have a Smartphone when we got them), but the video screen does have a memory stick that saves the videos, although we have to take it out and download whatever we want to keep. The video screen also has an intercom so that I can talk to someone at the door if I want to, whereas the light does not. We used to have a clear window in our old door, but when we got the new door, we had to get the security cameras so that we could see who was on the front porch without opening the door. We've not had any Jehova's Witnesses visit us since we put up the security cameras. I don't like the look of the security cameras, but I am pretty much stuck with them.

I really like the body color of the house. I agree that the trim is too pink. Are you going to repaint the whole house, or just the trim?