From what you've said, I'm guessing the best solution for you is to figure out what is really bugging you, and address that with the least possible work for the short term. Either match the grubby patches with the creamy colour, or paint it all so it matches the addition. You are in the busiest years of your life! You'll have more time later. Later, figure out what you want to do in the long term. Do it later. The only thing you want to avoid now is doing anything irreversible - like removing and discarding all the old moulding. Remove by all means, if that's what it takes to keep you sane, but don't discard! If your moulding has a nice profile, it is worth stripping even if you are going to repaint. Even if it is flat board, it's probably lovely old-growth wood, so give a future owner a chance even if you don't want to see it. You cannot strip "some" of the paint - it's pretty much all or nothing. But there is nothing forcing you to accept wood frames if you strip. Just clear-coat or shellac before you put more paint on, so a future owner can go that direction if desired. I have been living for 20 years with just the kind of paint you describe. Globby, put over unsanded filler, and drippy. Unbelievable that anyone could paint like this! It's on doors, moulding, and wainscoting. Actually we removed a lot of the moulding, but not all, and have done a lot of stripping. So I had some un-framed doors and windows for a long time, but they are almost all done. We will eventually strip more (kids are now grown), and probably repaint some of it. There is so much to do if you have an old house while the kids are small, we have always done whatever bugs us the most, and the rest, you just promise yourself you'll do it someday. What I have found the worst is living with half finished jobs - finished or unfinished is almost easier, though of course you have to get through the transition. And you know, someday comes before you know it. Enjoy the kids, put the time into them! One thing I have discovered is that painting over the drips and globs and ridges softens the old paint, so for about a day or two after your paint dries, you can relatively easily cut, with a utility knife, the worst offenders. That's been a lifesaver upstairs, where the attic is all beadboard that I am NEVER going to strip. I'm assuming I'm dealing with both latex and oil layers when this happens, so I hope it works for you. Karin L

Thanks, it is true that the sun in Florida influences the color palette! We live in the city of St Pete a few blocks from a lake, so it doesn't necessarily need to be beachy, and the houses on each side of us are yellow brick and light khaki. We do want to find a green-blue-gray for the body of the house, but a shade that is lighter than Restorative may be better given the heft of the house as you say. We are thinking the Sherwin Williams color "Valiant Blue" might be a better option. We don't want all of the window trim to be white, but instead want to find a color that will go well with the white sashes and grilles. We do like the haint blue porch ceilings, and if there is a way to incorporate this without it becoming too busy that would be great. Thanks again!

I'm fine with the shutters, but wish you had ones that fit. (They're too long.) Not a fan of the dark trim idea. The landscape needs to be redone. It is boring and a touch oppressive. If you want suggestions, move in closer with the camera, to about 1 1/2 car lengths from the house and take a series of slightly overlapping photos that pan from far left to far right, Include background space beyond each end of the house.

Thanks for everyone’s feedback. We are leaning towards doing a darker colour and I have ordered a few test pots. I have added painting the storm door to the list as well, great feedback and helpful to have other sets of eyes. Question - Should we paint the soffit and gutters as well? If so, same colour? Thank you.