Partnering with Seth Choate provided valuable local insights, making this an attractive and strategic investment.

How much should we allocate to demo such a structure and prepare it for development so that it's attractive to developers?

I know that I stand to make more money per renovation by just paying for the work, but I'm attracted to the idea of partnering with him for a few reasons.

The Oakland deal is attractive because you will be there to work the real estate post acquisition which will give you experience that makes you a better investor and a far stronger manager of your other real estate assets. 

And whats missing here is it can take a long time to resell land unless you have that ONE parcel that has value and you have it way under market to attract that very small buying pool who will cut you a check for the parcel.

To assume the simplest thing and answer your question: if you're having a hard time attracting buyers, its likely the property is overpriced for its current condition/location/overall etc. 

If you're considering it as a vacation spot as well, look for an area that excites you and offers interesting attractions.

Start thinking what makes a market attractive, and what I am trying to get out of this investment?

San Diego has clear regulations in place, and these areas attract tourists year-round.

You don't want to treat a GOOD tenant in a higher quality tenant the same as an IFFY tenant in a low quality rental because you won't attract or keep good tenants that way.