#2 is definitely A Closer Walk with Patsy Cline or Always…Patsy Cline (the cowboy boots, and she also sang "Three Cigarettes in an Ashtray" which is the newest clue they posted).
Oh yea, Bridges. But that's an Equity Tour isn't it... and with the tour on the road I doubt they have released the licensing rights for regional productions yet
Here is a bonus clue that was shared on social media, and it's suppose to be used in combination with with the honey from Clue #3 to guess the show. It has to be Matilda...