I'll be in San Diego in May for work related training and I don't know the area.
I'd like San Diego to be my home base for the whole stay and I'm thinking Ocean Beach will be the place to surf on work days. On the three free days I have in the area, I'll likely go as far north as Trestles or even Huntington to see what it's about.
I'm certainly not an advanced surfer but I'm not a danger to anybody and I know my place. Paddling 100 yards through white water and short period overhead sets in 45 degree water would be a no go for me here in NJ so when I read that a spot is a tough paddle I think twice.
I'll definitely bring the 3/2 with boots.
I don't expect I'll need the 5/4 with boots and gloves.
If you're not an advanced surfer, you'll be OK in OB from the Pier to Avalanches. Paddling out at the Jetty would probably not be advisable, there is an aggressive local crowd packed into a very tight takeoff area. You will be vibed and possibly punched. As well, I'd recommend staying away from the Cliffs.
Encinitas, Carlsbad and Oceanside provide wide open peaks with a mellow vibe and clean clear water.
Trestles? Ugggh, don't bother, unless you want to surf with 300 of your best "friends" and don't mind sharing your wave with 12 other aggro LA spazzes. HB? Sure. Consistent and a lot of waves between Newport River Jetties all the way up to the Pier. From the Pier to Huntington Cliffs, crowded....very crowded.
Your 3/2 and booties will be fine. A lot of guys wear 4/3's, but not necessary. Do NOT bring a 5/4 with gloves.
If the waves are "small", and you just want to paddle out in San diego, Mission has good waves and few crowds (long paddles though), and right up the street from mission is tourmaline, in PB, which has mellow waves and a lot of peaks (and virtually no paddle out). If there's "no" surf, you can usually find something fun to ride at scripps pier, with the la holla crowd. Cardiff isnt too far up the coast and its awesome if theres swell. last time I went it was the end of may and being a typical northeasterner, I paddled out for a couple sessions in trunks, but usually a 3/2, no boots necessary.