Looks like the inside wall of the rim has collapsed, leaving only the visible wall of the rim to support the spoke tension. Then the visible wall blew out, exposing the eyelet.
Often a tube will rupture as a result of the rim's inside wall collapsing.

The tire looks to have suffered an outer-ply delamination. Typically this happens only to aged or defective tires.
The three layers of tire casing under the tread are not woven, each ply has unidirectional threads which can allow the tube to blow outward between parallel threads and then burst.
This failure appears to involve two plies unless the single outer ply delaminated past the edge of the middle ply. Again though it's either advanced age or an insufficient-overlap defect that normally causes this to happen.
From the pictures, it appears that the old skinwall tire blew out, was then replaced with the Continental tire, and then the spoke eyelet pulled out(?).

The derailer hanger needs to be bent back to where the two pulleys both stay in a plane parallel to the sprockets even as the cage is rotated 90-degrees.

The rear wheel of a road bike is usually the most costly component to replace, and is the hardest to find in good, used condition since they are prone to failing before other major components do. So I always inspect any prospective purchase for rear wheel defects as much as anything else.