Hammer, I love that area too. Sounds like you are going to be living there a long time, so timing the market isn’t necessarily the most important thing to you.

Here are the plusses as I see them:
– close to downtown, and easy commute if you go over the hill, past the airport along the harbor. What a great drive every a.m!
– beach within walking distance
– nice community feel; people talk to their neighbors
– ‘alternative flavor’ – kinda hippie, kinda granola-y
– all the homes are different, and have nice size lots
– great restaurants, bars and shops
– People’s Market!
– Old Venice Cafe
– lots of homes being fixed up, and adding value to each block

Here are the negatives as I see them:
– some noise from the airport. I would go and stand on some of the streets you like, for an hour or so at a time, and see how bad the noise is. Stand there at night too, and see what it’s like. When looking at homes, see if the bedrooms have double-paned windows.
– The alternative flavor is sometimes a little too much – many drunks and drug addicts that sit down on the beach wall all day. Whose garden do they sleep in at night? Could your kids leave their bikes in the yard not locked up? There’s a transient factor too. It seems like the end of the 8 is the end of the road for a lot of people coming out West.

All in all, I think it’s still a great area, and the negatives maybe worth putting up with. If I were you, I’d try to find out a little more about the schools. I’ve heard the high school in Point Loma is pretty good, so keep asking around. At this point, you’ve got plenty of time to do your homework, and find out what you need to know. PD is right, even renting in the area, you’d learn a lot!

We might have the same taste, so also look into the following:

Mission Hills – great homes and architecture, nice lots, and windy streets with trees. On the edge of some canyons are magnificent views, but be aware that on some streets, you can really hear the roar of I-5 or the planes taking off at the airport. But, amazingly beautiful, with lots of old homes, and big established shady trees.

Kensington – nice community feel, great homes like the above, but pocketed between some shady neighborhoods. Weather is slightly warmer in Summer as it is more east, but it is right off the 15, and you could be downtown in minutes. Lots of good restaurants, etc too.

South Park – I think this is one of San Diego’s best kept secrets. Huge lots, Craftsmen and Spanish style homes, many overlooking Balboa Park, or the golf course, minutes from downtown, and home to San Diego’s hippest new restaurant, Vagabond. (Seriously, the types in there are some cool cats . And I don’t mean hipsters, I mean professionals with good jobs, but not plastic-y.)

Mt. Helix – a little further east, but some of San Diego’s oldest money, and many, many custom homes. Plus, the views are magnificent. Schools are good. But, a little harder to get in and out of. You’d soon learn the back roads. In fact there may be a way to jump on the 94 and head straight into downtown that I don’t know about. The neat thing about those homes up there is many have granny flats (so if you have aging parents, it’s kind of nice to know they could live with you, but not be on top of you.)

The funny thing about San Diego is that there are pockets all over the place. (I’m talking about below the 8.) So, if you don’t mind going a few blocks through bad stuff to get to good stuff, you can find beautiful homes.

I’ve heard Clairemont is very up and coming, and of course it’s ‘central’, but unless you’ve got an amazing view, and live on the edge of a canyon, I still think the homes are the worst types of tract homes ever built, and getting in and out is for the birds.

Hammer, best wishes on your planning. Great area, Point Loma/Sunset Cliffs is.

From experience, watch out what you lock yourself into: after our second child, my attorney wife said, “I want to stay home with the kids.” What a great decision it turned out to be. However, it did rather change the financial plan!

Life was much better and less hectic with my wife running the household and me bringing in the money. The kiddies got much better care — there is no better caregiver than a mother. Sure, we had to turn down the spending, but we could not be happier with how things have worked out.

Just food for thought.

Yeah, I tend to lump together Sunset Cliffs and OB just because it’s the same grocery stores, restaurants, gas stations etc. But, the further you are from the pier, the better. Thanks for clarifying Steve B.

As for the schools in South Park: unfortunately, I have no idea. I don’t have kids, and friends that were there, ended up moving to Mission Hills. I think the high school downtown was recently ranked among the top schools in SD, but I don’t know if you’d get your kids in there. And, I don’t know what high school kids go to in South Park. I think Mission Hills kids may go to Point Loma.

Overall, Point Loma, and Sunset Cliffs are more family-oriented. I live on the edge of Mission Hills now, and when I go for an evening run through the neighborhoods, I don’t see young kids, and families, I see older couples, or gay couples. But that’s also because I’m more on the Hillcrest side, which is a little more urban (as opposed to suburban), and definitely more gay.

But, definitely check out Mission Hills. Come up through the back part of Old Town. You’ll see plenty of nice long driveways! And when I’m there to watch the fireworks on the 4th, there are plenty of families in their yards.