I did the drive from LA pre-COVID and it wasn't so bad. Crossing the border into Mexico was easy, coming back was (unsurprisingly) more complicated, but manageable with NEXUS. Once you're out of Tijuana and on the toll road, the drive was easy. Apparently some folks suggest crossing at Tecate (instead of San Ysidro) and avoiding Tijuana altogether. You do need temporary Mexican auto insurance whether you are driving your own car or a rental car—I think you may be able to rent a car from some companies provided you purchase such insurance. Otherwise, I think your best bet would be flying into Tijuana and renting a car or hiring a driver from there. Or if you're local, you could take the trolley from SD down to the border, walk across, and arrange for a driver to meet you there.

Not sure what VdG is like these days, but we had an incredible time—the area is beautiful, the wine was better than I expected, and the food was really, really good. I'm itching to go back.