A significant part of our business requires us to do Flashing. Flashing should be over any piece of trim that runs horizontal. As stated in the title of this post. Caulking should never take the place of flashing! Its not a matter of if, but when its going to fail, and when it does fail, its going to exacerbate any underlying issue. This is a very common issue with painters trying to replace wood rot. Painters believe that they can just apply a piece of trim over the rotten siding at the bottom of a house and caulk it. Even worse yet at the middle sections of a two story home, where the seams meet on panel siding. This goes against every siding manufacture warranty. You are better off not doing anything, because at least the siding will be able to dry out.
WHEN SHOULD FLASHING BE USED?

What it boils down to is that flashing is one of the least expensive components to the
exterior of your house and offers the most protection. If you must cut cost, cut them elsewhere.
