Interesting this came up again, as I read this thread a few times as I was finally house shopping about a year ago. And we ended up in La Mesa. Near the village (on the south side of 8).
I won’t go much into it but its a long story, like most here: Years of bubble-watching, frustration at how my hometown seemed to change, friends thinking we were crazy for not getting in. We always liked uptown, but the prices remained out of our reach for anything but a teardown or an 800-sq. ft. 2br. We have two small children and I wasn’t going to get in a situation where I would grow out of a house in a few years.
So, we found La Mesa, or at least returned to it in our heads. With a home in the 300s in San Diego, there’s always give-and-take. Here’s what we love about it: quite, very few tracts, walkable downtown with independent businesses, large lots and relatively large houses, lots of craftsman and mid-century modern custom houses, trolley line to work, close to Downtown SD, great views in the hills, walking the hills in the morning, lots of life-long San Diegans, proximity to uptown and mid-city diversity (important to us).
Downsides is that it is really quiet – sleepy even. About 3 out of 10 houses are not kept up nice. University and El Cajon are not pretty streets, but if you like the hubub of urban life, they can be your lifeblood. Its quite warmer than OB, but not as hot as the rest of East County.
Schools are great. Cosmo’s rules. Riviera is a world-class hipster joint. 20-minute bike ride to Kensington. Terra moved from Hillcrest and is doing great. If you don’t think about housing costs, its easy to find fault with the town… but for us, considering bang-for-the-buck, it became hard to beat.