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?

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.

The gambrel is a unique style that at least provides more adequate clearance, re the upper roof line, than cape cods.

The last property I rehabbed had 15 year old wood framed Pella windows that were NEVER installed correctly & this was once a 'model home'.

All had suffered severe water damage & rot within the lower frames & sills regardless of any roofing overhang.

The studs around the window frames exhibited rot, as well as some of the flooring directly below the windows. The inner cavity of the drywall below the windows had significant mold.

(I often wonder how people live in a home with such obvious deterioration. But we stole the home because of its condition.)

I replaced 18 windows & all the doors (the doors were in the same condition). I made sure the studs were covered with 'waterproofing tape' & the joints had more than adequate silicon & the windows were vinyl clad.

On the new build I just did for my son I personally observed all window installs but the Pella slider door got me. It leaked inside due to blocked sill drainage holes. But their installer quickly rectified it.

Good luck

Thanks for the info @Pat L.   and @Joe Bertolino  

  Much appreciated!