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Hey Mike,
Your area is very desirable, you can over build a bit and get your money right out when the time comes to sell without any problems. The biggest issue I see is the foundation. No way they'll allow you to go up with out a new foundation. Be prepare to pay 12-15 K for fire sprinkler system. Your other issue is off street parking. That will almost dictate the allowable sq footage on the addition. You can dig into that basement but how far can you go? Depending on the engineering, the money might be the same as if you were to go up. The value is going up. Everyone wants a view of the ocean. I have taken an old Spanish and turned it into a large ultra modern home. There's a lot you can do here. The planning is going to take 3 months +. Yep, the city will try to rape you every corner you turn. Get with an architect and start talking about building details and cost. When I am involve from the very beginning of a project, I make sure the owner do not pay the architect in full unless he get the plans approved for construction. Before he submits that, you need to nail down cost with the builder. Once he submits it, you get to pay for those drawings so there's going back.
Where will you move to? The South bay is a beautiful place and safe to raise kids. Speaking of kids, my little boys still play with their rc cars when they are given a chance. The battery you gave us is still kicking. That's one tough little battery. Thanks again. Call me if you need to talk. I am more then happy to walk you through the process and give you my 2 cents.
Jeff
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