As previously mentioned your homes exterior wall penetrations are the next opportunity for leaks and damage. The windows and doors installation methods will determine how intensive your regular maintenance will need to be to be effective. The rule is water should be prevented from getting behind the walls cladding (siding) but even much more important it MUST be allowed to get out once it gets inside this protective outer skin.
So, first how do you protect the openings from the damaging effects of water? Starting last, on the outside of the finish a high quality sealant is needed at ALL location where water can enter and where dissimilar materials join.
Example: Use a high quality sealant at the joint of the window to the trim and the trim to the wall with most window and hard siding systems.
Example 2 When floating siding (like vinyl siding or other siding that is lightly hung or nailed) has been installed it gets a little tricky to properly seal and proper drainage is even more important.
Since you can’t see underneath after these items are installed you need to seal but still allow water to get out downslope if possible.