Mind the Gap

I figure, since it started raining again, that we really ought to do something about the gap.

This is the side of our house.  See the gap, under the gutter?

Yeah. Not so good.  It's caused water damage to both Brother-In-Law's room and the garage.

See the puckering paint?

Sak, freaking out about having to get the entire roof replaced, climbed out the skylight in BIL's room to assess the situation.

Though we are not professionals, we believe the problem being the curved angle of the bottom row of shingles.  Surely they are allowing water to pool up, and eventually leak down to the wall below?

In any case, Sak has been tasked with calling roofers for estimates.  I am hoping that there is a cheap solution to this problem, as bad as it sounds.  And yes, the gap in the wall was noted by our inspector in the beginning, we were just bad home-buyers and didn't think too much of it since no one else seemed to think of it as a deal breaker. The roof condition as a whole was listed as not too old, so I think this may be a one-spot problem.

By the way, I really wish our roof had eaves.  It's so weird and boxy without any! Maybe I'll just tape some plastic sheets up there until I can afford a nice roof with eaves?

Everyone's roof ready for the rainy season?