The cost of living out here is pretty high in terms of housing. I don’t know where you’re coming from, but it’s entirely possible you’ll be in for some sticker shock (have you already looked at anything?).
It used to be that the rental market was extremely tight. No vacancies anywhere. But I think that’s eased off in the past couple of years - there are lots of new home communities being built, and despite the insane costs, lots of people are taking the plunge and buying (myself included).
When people ask what communities are cool to live in, places like Pacific Beach, Ocean Beach and Hillcrest often come up. Those are places that have lots of things to do (restaurants, coffeehouses, nightclubs). I live in Clairemont, which is pretty central and is a decent neighborhood. It’s within 10-15 minutes drive to all 3 of those places, and it’s quiet at night, which is important to me.
Do you want city living? Suburbs? Vibrant neighborhood? Quiet place? That’s really going to factor in to where you might want to look.
I personally think you’d be VERY hard pressed to live here without a car. It really, really, really is going to depend on where you live and work. I could probably take a bus to work (I know there are lines that run between both, but it would probably take far longer than my relatively easy commute), but the trolley we have runs nowhere near my home or my work. There is something called The Coaster which is good if you live in North County (coastal) and work downtown. So it’s kind of dicey, and I would never want to rely on it.
I don’t know a think about sailing, but Mission Bay is home to lots of aquatic events. I’m pretty sure sailing is good, because if memory serves, the Americas Cup was held off our coast sometime ago. Or something… Anyway, San Diego has Comic-Con (which was just last weekend) which is known far and wide. There is a pretty good arts community in terms of little independent theaters - we’ve really gotten into that in the last year or so by going to Cygnet Theater, Sledgehammer Theater, etc. Outdoor activities are all around because the weather is so nice. So if you like to run, walk, bike, hike you’ve got options all over the place.
Do you have any specific questions? Do you already have a job lined up?
I found my last rental through apartments.com, so if you haven’t looked for a rental at all yet, I’d start there and take a look at what you’re going to be faced with. If you have questions about specific neighborhoods once you do that, post what neighborhoods you’re interested in, and I can tell you what I know.
Esprix also lives in town, so I’ll drop his name so if he searches on himself he’ll find this.