According to the Wikipedia page for KZOK-FM, this is a transmitter for that station. The station is Wikidata item Q6342548.

Trail here probably as it's a road parcel.

Waypoint 2 is here, but on the Parks & Recreation's own map, nearby, Waypoint 2 is shown as being further west, at the junction with Springridge Trail.

Westwood Road road end (public beach access) is here

Some of this is a public beach, that could do with being mapped here based on parcel data

I don't think Springridge Road veers off to the east like this. The land parcel for the road continues south.

I don't think even the COBI streets data matches reality here.

Trail north of here?

Public GPS tracks show route here south.