In all our Club Level stays at the Contemporary and Boadwalk Inn since online check-in has started we never used it and were always meet by a Cast Member when we arrived who took us to the lounge so we could check-in.
As for your requests I would e-mail them a second time to the Beach Club IPO Cast Members. For our Club Level reservation Boardwalk Inn we had requested a 4th floor room to be closer to the lounge since we are staying in their Deluxe Room and they also have some on the 3rd floor. Now we made that request when the reservation was made, however recently we also mentioned it to their IPO Cast Members in an e-mail. Well they e-mailed us back and said they will do the best they can to accomodate us, then also mentioned it's a request and nothing more.