I live in Orange County, next to Los Angeles. Prices are high. I had a condo in Los Angeles that incurred significant losses during the burst, so that sucked. OC is priced similar to Los Angeles but offers slightly newer and bigger homes for the dollar, but it's still ridiculously expensive compared to other parts of the country. I bought during the burst, so I've already made a good amount on this home, with a jumbo loan that's still cheaper than what people are charging for rent in my neighborhood including property tax, I'm contemplating renting out and buying another home to live in. Even if the housing market dips again, I should be fine since we bought relatively cheap. When I retire I'd like to think that my wife and I would either sell one house and retire in the other, or just sell them both and live in a maintenance free apartment or gated condo community and use the money to travel during our golden years.
Another possibility is commercial property or a multi-unit rental complex. I haven't looked much into it yet, but it would be nice to have passive income be the cherry on top of our retirement and pension. An apartment complex sounds like a huge pain in the ass though. Again, lots of research ahead.
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