Regarding the HPILPT, the AIM says, "The holding pattern maneuver is completed when the aircraft is established on the inbound course after executing the appropriate entry." I've always taken that to mean once you cross the fix the second time (first to start the entry, second to continue inbound), you've done a "holding maneuver", and that should fill the "holding" square in 61.57(c) -- and nobody in the FAA has ever disagreed with me (not that I'm going to put this question before the Chief Counsel unless someone from Flight Standards says otherwise, and so far, none of them have).
As for me, I get plenty of HPILPT's in both my own plane, and enough regular holds practicing missed approaches in actual conditions with my trainees that never have to worry about how I'm going to fill this particular square.