Intro
Keeping moisture from infiltrating where it can damage sheathing and the back of siding is relatively simple. The usual problems are inadequate or poorly installed caulking around windows, doors, gable trims, and other joints. Take the time to inspect all the places where water could get in and apply high-quality caulk where needed. The exception is vinyl siding, which should be caulked only in those places where vinyl pieces abut wood or metal surfaces.
Also check your home's flashings. Check whether you have flashings where they are needed--above doors and windows, at vertical joints of panel or board-and-batten siding, and at the top of a water table. If you are missing some flashings, consult with a professional to see if you should remove siding pieces to install flashing or if you should simply caulk the joint well.
Prestart Checklist
Time
An hour or two to replace damaged flashing or apply caulk around several windows or doors
Tools
Caulking gun, tin snips, lineman's pliers, flat pry bar, hammer
Skills
Caulking, a skill that you can learn with 15 minutes or so of practice
Prep
Inspect around windows, doors, and trim boards to see if you need to replace flashings or apply caulk.
Materials
High-quality exterior caulk, flashings as needed, nails