We have a 1930s wood shingled house. We've known since we moved in 6+ years ago that we'd eventually repaint; the color is not one we would have chosen ourselves. But the previous painter did a really good job, and the paint is still in good shape. The trim and doors, however, are peeling/cracking in spots and are going to need repainting very soon.

I know hiring someone to paint will be hugely expensive, especially since we live in the Boston area. Is it better to just do the trim separately from the rest of the house, since that's the only part that really needs it now? Or will it be more cost effective to do the whole house at once if we're going to repaint the whole thing in the next 5 years anyway? If we wait until the paint on the body of the house is peeling and requires a lot of scraping and repair, will it be a lot more expensive than repainting now when the paint is in good shape?

thanks!