I did a trim job in one of those up class areas and the home owner was a pain. I had to replace a few of the boards as they where rotten. Then had to peel the paint off, The home owner treid painting over oil based. Here are the two windows I had to do.
The home owner wanted the trim to be painted one shade off of the house color. I treid to get them to make it a color that would allow the trim to stand out, but they did not like that idea. Here are the after pics. Sorry the pics are not the best.