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!