After a new home is painted by a painting contractor and the wood shrinks along with the caulk, is it normal to need to re-caulk and/or repaint before the first year?

With the settling, you get in a new house and as the wood dries and shrinks, you’re bound to have some places that will need to be touched up with more caulk and paint. Usually, after the first year, you won’t have any more shrinkage. Make sure your painting contractor uses a good elastomeric caulk that is flexible and will withstand some movement in the joint.