Question for Puppy if/when you read this.....Given her seemingly obvious attempts at reassuring herself that I'm attracted to her, do you think it's time for me to try to initiate some physical contact
YES. However, if you get rejected, it's critical that you laugh it off with good humor -- no poutiness -- and move on. SOME sort of a "180" from how you may have handled sexual rejection in the past.
She is either trying to draw you in, because she wants to ML with you, or she's playing some sick mind game. About time to call her on it and find out which, methinks.