All in one trip. My first wife, Marilyn was 5'3" and overweight. After our second dive one day I told her I would carry the tank on my back and both gear bags up the hill, then come back for the other tanks. By the time I huffed and puffed my way back from the car, she was already at the top of the cliff with three tanks. I was impressed!
The last time I dived from the beach there was just a free dive. Even with a lighter weight belt and no tank I was breathing pretty heavily by the time I got back up.
It looks worse than it is, though. There are some goat trails in P.V. that are tougher. Honeymoon Cove has a small section near the too that you have to sit and slide past. Flat Rock is a long trail, with one section barely wide enough for your feet. I was making a night dive there once when my weight belt slid down to my ankles, right at the narrow section. I had to pull it up without leaning sideways.
Haggerty's used to have a truck tire inner tube to lower yourself over the bottom section. Now there is some polypro line. In the late 90s someone constructed a very nice set of wooden steps down to the rocks on the south side of Malaga Cove. It only lasted a month or so until some idiot painted graffiti on it and the owner removed the stairs.
I used to climb the trails around Palos Verdes nearly every weekend, including the pipe near the Avalon and the Dominator hike at Lunada Bay. When I was feeling lazy I would head down to Laguna Beach for some easy sand diving.