But old houses are really only good if they are located in a community with historic charm, like the beach communities dotting the California coast, or a nice old city like Orange, Pasadena, etc. 

I maybe moving my family to Orange County.

We have never participated in a Joint Venture ourselves, but have a few people that have asked us about getting in on some of our deals in Orange County, therefore; I'm very interested in how others structure them.

I think in Orange County there are a lot of buyers waiting to pounce on the right opportunity.

I don’t know about you, but I don’t look good in an orange jumpsuit.  

Then they say stupid things like "we buried Aunt Edna in the backyard because she loved the Orange Tree" and buyers say stupid things like "What an ugly collection of Urns on the mantle" when Fluffy the favored cat has her ashes in the Urn.

There are not very many people that have developed pocket neighborhoods in Portland, but if you want to talk to two of the best then I would try reaching out to @Mark Desbrow at Green Light Development who has done two pocket neighborhoods I believe, as well as Eli Spevak from Orange Splot who does amazingly creative work and is also a pioneer of pocket neighborhoods in Portland.Currently there is a proposal in Portland called the Residential Infill Project that seeks to provide a path for more pocket neighborhoods to be developed, but it is a rocky road and some of the latest versions have really dwindled down the policy's potential effectiveness.If you want to check out another great pocket neighborhood while you're in town but want to escape Portland go to White Salmon, WA in the Gorge.

I currently live in NY and work in Manhattan so I was considering Essex County (East Orange, Orange, or Upper Irvington) for the low cost of entry.

This will be a VA loan, 30 year fixed, in Orange County, CA. 

Outer CA areas as well as LA and orange co, and many other states, got hammered much harder, -30 to 50%.