What kind of paint??

[Big pig]

Caulk everything first, then prime it, then several coats of good exterior no gloss/flat paint

This. I buy the cheap returned exterior paint at lowes/Home Depot. I paint inside dark colors and multiple coats on outside. I spray camo patterns for me when I am done. I actually am "O/C" enough to paint frame before I screw on plywood.
They will last for many years with good paint jobs.

BP

[Big pig]

Make sure to heavy paint edges. Water will wick up down and sideways

I also have used "gutters" above Windows and door.