I've also spoke to some people with aspirations of building tiny home villages...

Instead of looking in Beacon Hill and Alta Vista, look at Los Angeles Heights or Dellview & Greenhill Village. 

It takes a village to raise a child

Society Hill, maybe Lexington Village, another development off Rues Lane near Route 18, not far from Churchill School.  

There shouldn't be any tax event in your scenario.With respect to Google Village, it won't happen overnight.

So i was specifically looking in the village of "West Milwaukee" so on Greenfield Ave and east of Miller Parkway.

I took my client out there 3 times once with a structural engineer, once a furnace guy and once with village building inspector (don't ask).

And its not all about the MLS - I have plenty of clients that call in reference to private transactions as well.Me personally - tell me an address of a property in Little Village (Chicago), the most basic of details, and your goals, and I can tell you if its worth it for you to see/consider further.

Wicker Park, Ukrainian Village)  2 story (+basement) SFRs are available for sub $400k and sell in excess of $1M when rehabbed with high end finishes.

I am from Englewood/Greenwood Village (college n Greeley), but have been living on The Big Island in Hi for the past 20+ years.