Diamond Heights is definitely the best. Really love living here. I'll say it's way better than those Twin Peaks neighborhoods (Midtown Terrace / Forest Knolls / Golden Gate Heights).. (1) It's on the border of the fog, being protected by the 2 highest mountains in the city, Twin Peaks in the north and Mount Davidson in the West. So the fog from the Pacific Ocean usually just stops around those 2 mountains during the day, with a little slice floating to Diamond Heights from time to time. Just during night time, Diamond Heights can be a little foggier... In most days of a year, you can actually oversee Daly City and San Bruno Mountain -- the areas in the south in fogs in the far, but you got clear sky and bright stars in Diamond Heights. So the fog is not that a big issue up here. It can be just a little too windy sometimes. (2) Also, it's surrounded by all the safe neighborhoods. Glen Park (south), Noe Valley (east), Twin Peaks/Midtown Terrace (north), the Canyon (west). With that being said, it's actually much safer than Noe Valley, which is way too close to Mission and Castro Districts. Then Diamond Heights is not that creepy quiet like in Twin Peaks, because it got some condos and townhouses up here. I think the development back then kind of intentionally mixed different types of properties. (3) When you do daily grocery shopping, Safeway and Walgreens are in walking distance. When you wanna dine out, hey it's so close to Freeway 280. Just hop in a car, and you'll be in Daly City/South City/Millbrae really fast. From Diamond Heights to Freeway, you don't need to drive through all those stop signs and neighborhoods. Just Diamond Heights Blvd -> Elk St -> Bosworth St -> and voila. (4) The most important thing is, Diamond Heights is so clean and organized with wide and well paved streets, and zero ugly power lines over your head. I think it's because everything was already planned out first when the city got this development back in 1960s... If you go to Potrero Hill, Bernal Heights and Mira Loma (Mount Davidson) and see those bumpy narrow streets, you'll know what I mean. Totally different looks. Also Diamond Heights comes with bright and nice street lights for almost every street at night... Many other residential areas in the city or San Mateo county are too dark at night (no street lights, and all count on lights from people's houses if you walk at night). So really love the safe vibe at night in Diamond Heights.
I loved going to Glen Canyon Park growing up there is also an awesome park behind the Safeway that connects to the Canyon trails that is pretty sweet. Great area