HOW DO YOU PLAN TO PREPARE THE SURFACE FOR PAINTING? Proper prep work is the key to a long-lasting paint job. Make sure your contractor has a clear plan for washing, scraping, and sanding the surface.
WILL YOU PRIME BEFORE CAULKING AND PAINTING? All bare surfaces require a primer; previously painted surfaces usually do not require primer.
WHAT AREAS ARE YOU PLANNING TO CAULK? The most common cause of paint failure is due to moisture from water getting behind the paint. For that reason caulking all joints, seams, gaps, and cracks in the surface is a must to ensure a tight seal.
WHAT KIND OF PAINT DO YOU PLAN TO USE? Good quality paint will be recommended by good painters, you probably don't need the most expensive product, but don't cheap out on this either. Make sure the painter can explain the benefits of the paint they are recommending and ask for documentation of any manufacturers warranty info and product data.