There are lots of towns in CT with median home prices well over 300k and awesome school districts (for locals, think West Hartford, Farmington, Orange, Monroe) where you can pick up a scraggler for 150-200k, give it some minor/straightforward rehab (usually kitchen & bath updating, a new face, and just a lot of lipstick) for under 50k, and all of its comps are selling for 350k+. 

You realize you could say "Every Friday is required to wear orange day" and they would just nod. 

Bringing in some charts that include the periphery of Upper King just below crosstown is comparing apples and oranges.

Yet I would still argue Orange County is still a great place to invest.

I like the idea of buying a 4 plex first and live in 1 but, 4 plex in Orange county, CA just costs way too much.

Virtually every source that tracks return on buy n hold shows San Francisco, Los Angeles, San Diego, and Orange County have produced the highest return for buy n hold investors virtually every decade starting in the 1970s.  

I mainly appraise single-family homes in Orange County and apartment buildings in Los Angeles County.

You can see it in any other desirable locale be it LA, SF, Orange County etc. 

They also have monthly get togethers in Saint Augustine for breakfast and another for lunch at Whiteys Fish Camp in Orange Park. 

I am by no means going in blind or rushing the process.As stated in my original post I am fully aware of zoning issues and I am looking anywhere from Charlotte county to Orange County primarily focusing on Sarasota county to buy land.