Hello all,
I'm new here, but I thought I'd jump in with a post. This is my backyard and where I learned to fly, with most of my flying done out of KPAO and KRHV and a little out of KSQL. I'm also a low-time pilot with only about 300 hours. I'm a member at both West Valley Flying Club at KPAO/KSQL and Aerodynamic Aviation at KRHV/KMRY/KSNS but I don't own yet. KHAF, the closest airport to Pacifica, doesn't have any rental outfits that I'm aware of. KSQL is the closest to both Pacifica and San Francisco.
This is a fantastic place to fly. If you're willing to go the OpenAirplane route, San Carlos Flight Center out of KSQL is a fantastic club that offers aircraft through OpenAirplane. TradeWinds out of KRHV does, as well, but I have no experience with them. To be honest, I haven't heard any major complaints about any of the flight clubs at KPAO or KSQL.
Whether you do or do not do OpenAirplane, I suggest a CFI for your first flight no matter what, especially at KSQL. It's so close to KSFO and the floors of the Bravo so low that it's a terrible place to get behind the airplane. Get a Bay Tour with an instructor and the next one on your own is actually quite easy. A little more challenging is the Oakland Transition, so try to get the instructor to show you that, too. (The San Jose Midfield is easy if you're polished on the radio. Eight or nine frequencies in the 15 minutes flying from KPAO to KRHV, but few restrictions.)
Recommended destinations:
KAPC - Spend a day in wine country. If it's just for lunch, Napa Jet Center can usually supply you with a car for free. Buy some fuel, keep 'em in business.
KMRY - Monterey is great, as well. See the aquarium, have a seafood lunch. Del Monte Aviation will lend you a car for 10 or 15 gallons of gas (can't remember which).
KHAF - Park at the south parking and walk into town. Lots of great food.
Bay Tour - See all the sights! (Yes, you'll actually ask Ground for a "Bay Tour". That's actually the "destination" in the system.)
My most recent Bay Tour with a couple of my interns. I'm not a photog, but one of the interns is, so I got a couple interesting shots. I've always wanted my own shot of Sutro Tower poking through the fog, and now I have one. Unfortunately, the low clouds meant no shots of SF.
https://arnoha.smugmug.com/Airplanes/Interns-2015/n-7H2x95/
And, yes, that was all VFR legal. There are advantages to Bravo.
Happy to answer what questions I can about the area.