Hi Matthew,
My sincere apologies for the delay in my response, I’ve been caught up in a few things in the community that need my attention the past few days.
I’ve listened to where the words puzzles are for at least a few times, and below are my guesses:
21:09 “Both are…”
I have a feeling this is an unfinished sentence with the unsaid part well-understood based on the part leading up to this part, i.e. “the two difficulties in healing and transforming ourselves” that Dr. Larry was talking about. So if “Both are…” is to be said in full, it might be “Both [views and habit energies] are [Buddhist technical terms].” Please feel free to correct me here 
38:53 " 'cause when it hits the shore, the part of the grandmother in me says, 'It’s all over but the shouting."
54:27 “Let me put these away.”
I believe Dr. Larry said this as he was moving his pair of eyeglasses from the one hand he was using to “draw” in the air the depth of what he was saying – to the other, free hand of his.
54:49 “and… ya know”
The five skandhas are (1) body, (2) feelings, (3) perceptions, (4) mental formations, and (5) consciousness. The (2), (3), (4), and (5) are the mind. So, I guess Dr. Larry said “The five skandhas, body, mind, and… ya know”.
1:02:33 “When I first started doing this, giant fear just like… oohhhh… really puffed. It puffed like movies.”
These are my best guesses. Let me know what you think
I hope it helps!
Thank you very much, dear Matthew

Tuyen