Odd roof/siding construction any repair ideas?

[Andrew S.]

I have a question for the construction-and-repair inclined in the BP community:  I'm contemplating the property shown below.  The style looks very odd to me and in fact, as one might guess, there are water intrusion problems around all the windows (upstairs and downstairs).  Is this simply a design/architectural flaw or is there a solution to this?  Are there any window options available that can actually deal with the fact that basically there is no roof (or at least no overhang) to protect against the elements?

[Joe Bertolino]

It is called a gambrel style roof. You can google and get a ton of info. I have a gambrel style cabin in Tahoe but I have not had any issues.