@Dan H. you're contradicting yourself. how do you know San Diego isn't going to be like Detroit? Detroit was doing pretty well too, you know. How do you know there won't be a downturn in the real estate market near term and there will be drop in value. Sure, maybe you outperformed and did well before, that doesn't mean it will continue to do so, and it doesn't mean where you will invest will not explode.
You have $200K equity and and even if you $50K closing cost that $150K which you WILL DEFINITELY find a property that cashflows more than $600 a month. YES, I'm pretty comfortable saying that as long as you don't blindly invest in a terrible property you can beat $600 cashflow any day. Maybe you invest in SD so you are biased. If you want to play the appreciation game, why dont you invest in San Fran or NY instead? I bet you their appreciation beats San Diego for sure. My primary resident in NY has appreciated by 60% in past 4 years. Yeah if he wants to play the appreciation game, i think he should definitely sell the property and invest in NY.
Like I said, if he really thinks San Diego property is going to keep going up, he can cash refi and use that to invest elsewhere. until you pull out equity and realize it, that number is only on paper and doesn't mean anything. more and more principal payments you make, less and less tax credits you get from interest expense. Always better to keep refinancing, take cash out, and use the power of leverage in my personal opinion.