For what it is worth. I have always jumped in with my camera and occasionally reenter with my camera (clipped to my chest strap D-rings and scooter/crotch ring). But usually I hand it to a deck hand who I try to discuss with them my preferences beforehand. Most times they do their best to accommodate. I provide instruction to NOT put my camera in the "camera bucket" but to instead place it in my soft cooler bag (Sam's Club).
Giant stride entries from normal heights are easy, I can raise the camera as I enter to reduce shock to the system. Upon return, the crew is going to grab anything and everything they can quickly. Usually a strobe arm despite my pointing to them where I wish for them to lift. So, I bought a Nauticam braided piece that I clip between my strobe arms and the crew automatically goes for it. Happy day!
Here you can see the two bolt snaps on the arm joints for connecting to my chest D-rings and the small tether and bolt snap on the handle for the scooter ring. The deadman (blue) tether is connected as I step to the platform and disconnected as the crew takes my camera upon reentry to the boat. The Nauticam handle (white) is clipped to a D-ring during the dive and upon dive completion, I rotate the strobe arms up, clip the two arm bolt snaps together and attach the Nauticam handle for the crew's target fixation need. I also have the two silicone elastic bands (could be 4mm bungee even better) from the strobe clamp to the lower arm clamps. This ties the camera rig together (for both entry and exit).
I have had cameras dropped into the ocean, I have had water contact optics knocked off by crew mishandling, I have had strobe arms disconnect, I have had domes scratched. So, I try to eliminate those things by discussion before hand and my rigging of the system. I keep my WWL-1 port cover with me, clipped off to my scooter ring, it is on during entry and exit. Your system will get some scratches and scuffs during use, otherwise leave it at home, diving is rough. Not to mention the scuffs and scratches on me!
I will say, with my camera clipped off to my chest D-rings and scooter ring, I can usually reenter the boat via a ladder with the camera as long as it is not too rough. If the ladder is slamming up and down, best to hand off to the deck mate.