The hoop is attached.
Consider that the friction force is given by:
F = μ·N
= μ·m·g·cosθ
We also know, considering the forces of the whole system, that:
F = -m·a + m·g·sinθ
and
a = (1/2)·g·sinθ
Therefore:
-(1/2)·m·g·sinθ + m·g·sinθ = μ·m·g·cosθ
(1/2)·m·g·sinθ = μ·m·g·cosθ
μ = (1/2)·m·g·sinθ / m·g·cosθ
= (1/2)·tanθ
Now, solve for θ:
θ = tan⁻¹(2·μ)
= tan⁻¹(2·0.9)
= 61°
Therefore, the maximum angle you could ride down without worrying about skidding is 61°.