Are you replacing the roof at this time?

You can't go wrong with painted brick in a blue/grey with white trim.

I was hoping we could repaint the roof a lighter colour. Thoughts?
What about window trim colours in cream?

You don't paint a roof. You replace it. Same with all of the rest of the $$$$ changes you are talking about here. What yu have as a wonderful charm to it. I wouldn't be so quick to throw away money on anything but that fence. It needs to be replaced. Maybe with a hacienda style adobe fence. That would suit the style of the home.

Try the Sherwin Williams paint visualizer to see what trim colors might look good. If the roof needs replacing, then you can change at least one major feature of your house.