Update: Hopefully the power plug situation will be solved, as I have FINALLY found an obscure customer feedback comment on some site that said the cradle I am using does not allow the power cord enough room to seat. I checked this out, and it is true. I had not noticed that before. I circled the piece that causes the problem in the below picture. I cut out this piece and the cord seats MUCH better. If this weekend's ride happens as planned, I will hopefully be reporting back my success.
REMOVE THIS PIECE
