Are you a painting contractor? I need some advice.

[jeff47]

1. It depends.

(Former general contractor, not officially a painter and hired them for all but the smallest jobs)

It depends on how bad the paint is. If the new paint is blistering and coming off, but the old layers of paint are more-or-less covering the wood, it should be OK.

What you're worried about is bare wood getting soaking wet and not drying quickly. If the paint looks lousy, but it's still keeping most of the water from reaching the wood, you shouldn't see damage from one winter.

If you do have some really exposed areas, you could hire some local unskilled folks and tell them to slap some cheap paint on those areas. It won't look good, and it won't last long, but it'll protect the wood for this winter.

As for "this late in the season", what you need is a couple days without rain to do the work, followed by two or three days above about 40 degrees. So you've still got a good amount of time to get the "full" job done.