I grew up outside San Diego in a town called Ramona. It's actually just through the canyon (about 25-30 minutes) from Lakeside. Lakeside is....well, definitely a "hicktown". There isn't much there, that I remember. It could have changed drastically in the housing boom with lots more grocery store choices than I remember. It's fairly inland, so it doesn't have the stereotypical beach weather that San Diego is famous for. The summers are going to be HOT. You'll be somewhat near San Diego State (SDSU), which can be a plus and a minus.
My brother lived in Pacific Beach (everyone calls it "PB") for a few years and absolutely loved it. He rented a 1br/1ba apartment about 1/2 block from the beach for $850/month, and that was about 8 years ago. So, expensive. He also grew very tired of all the beach-goers. It created a lot of traffic on a daily basis, and tourists don't always make the best neighbors because they don't have to live with what is left behind. But there seemed to be a genuine sense of community amongst the residents, which is harder to find in the outlying suburbs (like Lakeside) since the housing boom happened and lots of people flocked to the outskirts of San Diego. In PB you are fairly close to downtown San Diego, which means lots of parks, things to do, great bike riding, etc.
It looks like La Jolla borders where the PB school is, which is definitely uber-expensive and very non-Mustachian. It's right near University of San Diego (USD), which again, could be a plus or minus. Probably better than living near San Diego State because it's a private university and the reputation is much calmer than SDSU. But it also might lack some of the diversity of a state school.
I've also heard really good things about Point Loma, but it might be farther from your daughter's school than you'd like.
If you choose the PB area, you also are super close to Balboa Park, which is just amazing for kids. The zoo, science center, galleries, museums, and lots of gardens and indie artists.
Not sure if any of that helped since I don't have a ton of specifics. I've spent a lot of time in San Diego visiting family and for work. We also attend Comic Con every summer and love to hunt and peck around the gaslamp district for fun stuff to do while we're there that gets us away from the crowds. So, a lot of my knowledge is a little shallow.
Good luck!