How to deal with paint that peels after 2 or 3 years in the same places.

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gabagoo

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This is exterior paint. The house originally had oil based paint from new, and up until 3 years ago I would always repaint with oil based. I hired a contractor to switch over to latex and everywhere he painted is fine except these 2 areas that also gave me issues for the last 15 years or so. The garage has a flat roof and there is an 8" wood molding that sits just below the roof line. I am pretty sure it is mdf. There are 2 spots that the paint just starts to peel off forcing me to repaint these areas every 2 or 3 years... Everywhere else on the house that the paint was used is perfect. I am going to scrape it down and sand it once again but wonder why these 2 areas never accept paint for long term? What can I do to remedy this?
 
Peeling paint is often a sign of moisture trying to force its way out through the paint. In a house with a crawlspace it can indicate that the bare dirt floor isn't covered completely with plastic.

Is there a place near here where water could be getting into the space? j
 
the flat roof has these formed sheets of tin that are about 2 feet wide on the flat top and then they turn 90 degrees and curve under the edge and meet up with the mdf. here is a pic off google earth...not the clearest but I circled one of the continual areas that will peel.
 

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Look for flashing along the wall or a caulk joint that's failed. Silicone is often used and not the correct product for use outdoors joining dissimilar surfaces.
 
How does the rain water get off that flat roof? That trouble area prolly should be covered with vinyl or aluminum siding since the rest of the house is permanent brick.
My house was painted 41 years ago with premium oil based paint and still looks newly painted except for some areas where moisture was coming out from an unrealized roof leak...
 
How does the rain water get off that flat roof? That trouble area prolly should be covered with vinyl or aluminum siding since the rest of the house is permanent brick.
My house was painted 41 years ago with premium oil based paint and still looks newly painted except for some areas where moisture was coming out from an unrealized roof leak...
There is a drain in the middle of the roof. It works quite well, although there are a few area that pool a bit.
 
I assume the drain stops working in freezing weather?
yes but when it warms up the water never comes over the sides. There is a drop of about 3" from the side pieces that encompass the 3 sides of the garage roof. I am convinced that there is something about that mdf that just won't accept paint as it is always the same 2 places that heavily peel and lift where every where else that was painted is just fine. I will scrape it all down and reprimer and paint it myself this time.
 
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