If you liked your home and you like San Diego I would recommend that you pay off the house. If you consider the costs and inconvenience of buying and selling plus the loss of a low property tax basis, I think you would find that it would take a really large price drop to come out ahead.
On the other hand you have thrown the possible Orange County Move into the equation. How certain is that move?
I believe the things that Rich Tuscano says about a housing decline in San Diego. Am I positive the crash is going to happen? Absolutely not. I also believed some other smart people that told me CDMA technology would dominate the worldwide cell phone business and Qualcom was a great buy at 30% more than today’s selling price.
There are no sure things when it comes to investing. We could have another bout of raging inflation or we could replace a large number of poor peoble with a large number of rich ones. The direction of markets cannot be reduced to mathmatics.
A house is a very special thing even to someone who works 80 hours per week. Living in a rental is just not the same.
Would you have more money in five years if you sell and rent? Probably. Is it worth the agravation and risk?
If prices actually crash, that house in the beach area of Orange County will drop a great deal more than your Chula Vista house. The spread between your present home ant the O.C. home could easily shrink several hundred thousand dollars. I for one would be happy with that improvement. I do not like to speculate on my personal residence.
My recommendation is stay where you are until you are ready to move.