mmmm, looks like Trail Mix up in pic #1
Not to be critical, but in pic #1 I thought that maybe you disconnected the downspout from the gutter, but I don't see a drop outlet there. Would think even with the camera angle it would show up somewhat.
Also in the same pic, just an FYI, it's best not to have the end cap of a gutter tight up against a house wall. Leaving a 1/4 - 3/8" air space between them will allow wood to dry out, and not rot over time.
EDIT- looking at pic again, maybe the "wet spot" is a shadow of the gutter on the wood wall from a camera flash, maybe there IS a space there, can't tell now.
I think I would have a heck of a time cleaning those gutters, it looks like a lot of gutter is tucked under the roof edge, leaving just a narrow slot to try to reach into. Is that the style in your area? Or is it an improperly mounted or missing fascia board behind it? Unusual to see that amount of tuck-under.
The cliff looks fine