I've done it, but I'm in Phoenix.
From SD, it will be a tough run. AM flight to SD, plan 2 hours to get over the border, 2 at center, 2 to get back... you certainly won't always need all that time, but you do have to plan for it. 6 hour pad, 2 hour airport wait, PM flight out.
8 hour window. Doable. It's a lot to ask, really it depends on flight schedules.
I'm also figuring that you'll do the trolley and shuttle to a taxi. Otherwise, you'll also have to calculate in the OCC shuttle schedule.