EVERYONE I've ever dove with enters the water with the reg in their mouth. If you don't... well then you can not breath UW which defeats the point of all that equipment on your back!
I think if you knew any dive guide/instructors who started white water canoeing at age 5, competitive swimming and free diving at age 6, scuba and cliff diving at age 7, lifeguarding at age 15, have a significant number of 1-2.5 mile rough water ocean swim competitions under their belt and numerous kayak or surfing spills in double overhead surf (or any other combination of serious water experience) you would come to the conclusion that many divers successfully enter the water without reg or snorkel in their mouth.
When guiding scooter dives with overhead surf at the beach entry/exit, if I can't shout instructions/warnings at any moment I may very well not get any tip after the dive; can't have that! On dive boats I only always most of the time enter with a reg if the captain/owner forces me to. Unless I am paralized upon impact with the water I can always just swim back up to the surface, even 8 #'s over-weighted with no air in my BC. Most of the time I would prefer to enter with my mask around my neck as well, to rinse the antifog.

Finally, if the Cardinal Rule of scuba diving is Never Hold Your Breath, how do divers equalize their ears on descent?
