Having lived in this cottage for the past 31 yrs I knew what I needed/wanted for the yard as far as rainfall preparation. We got shady patios and roofs built and took the good advice of the contractor for a drainage pipe to the street. The yard was graded toward drainage installed underground (under the garage sidewalk) with pipe leading to the street -- but deluge rain is too fast and furious all at once so the draining is slower than we like -- but it does eventually drain out to the street. As long as the house doesn't get flooded we're happy so it's doing the job. Regular rainfall drainage is not a problem but this past week of fast and furious deluge and then it's over is so typical for us at least once every decade. Just can't let the chickens out to forage until the water subsides.
The only real problem with drainage for now is inside the raised garden bed - my newest bed isn't complete yet so it got several inches of rain water and took longer to soak into the ground - the sideboards kept the rain water from leaking onto the patio so we're glad we had board installed before the rain - it held back several inches of clean rain water.
I'm not sure what you usually do in the states, but what about staining/oiling instead of painting to keep the rustic look going 
