Free fall vs falling on incline of rotating bodies

When the angle of incine is $90^o$ there can be no friction acting on the objects. That is because kinetic friction between two surfaces is directly proportional to normal force between them. When the incline is vertical, there will be no normal reaction since there is no horizontal component of the falling bodies.

When they are rolling down an incline, the frictional force on a loop is greater than that on a sphere. Thats why the sphere is faster. When falling, there is no frictional force, and thus they both fall with the same acceleration (irrespective of whether they are already rotating or not).

If you are requiring no slipping at all, even in the case of a $90^circ$ incline, then the sphere would still "fall" faster than the hoop. This is because rolling without slipping requires a friction force. Of course, the larger the incline angle the easier it is for slipping to occur, and without any other forces at play at $90^circ$ you will have to have "slipping" (really just falling, with both objects then hitting the ground at the same time). But if you had some other force pushing the objects against the $90^circ$ incline then they would not "fall" at the same rate.

Indeed, one can show that the acceleration of each object is given by $$a=frac{gsintheta}{1+gamma}$$ where $gamma$ is obtained from the moment of inertia of the object $I=gamma mR^2$. Of course, when $theta=90^circ$ this acceleration still depends on $gamma$, but this is because we have assumed rolling without slipping in the first place. In reality in order to achieve rolling without slipping on a $90^circ$ incline one would need to apply a force completely perpendicular to the incline to prevent slipping (and a force in this direction will not change the acceleration given above). Without this force you will essentially have no friction force, and hence you will have free fall.