(We intend to subdivide the land for 10 additional acreages (3 acres per code), but that will be another post.) 

I would pursue historic rehabilitation, mainly to qualify for Historic Tax Credits (Federal 20% and State 20%) unless I am obligated to abide by strict historic preservation rules which I don't believe I am.As you point out, I'm in contact with the City as well as Engineers/Architects specialized this area.I'd appreciate hearing from anyone with first hand experience in any of these areas, historic rehabilitation, adaptive reuse, conversions.

Do you have to be in a particular zip code or neighborhood to work with the LHA?

There is a convergence of people being willing to live in smaller/alternative living situations (new generation) and the technology to make it happen (smart homes are here but alternative building techniques have been slow to catch on due to outdates building codes- but the technology is there) I think we are going to see some massive shifts in the next 20 years.

Other times they are required to produce the information to certain parties per state code.

@Steven Stokes If the money investor is strictly passive, it is still a security. 

Is there a website that compares price estimate to rent estimate whether for a specific property or zip code/neighborhood?

Signage - If automating the facility have clean, clear and concise signage with QR Codes telling customers that they can rent on your website.3.

You may want to check out the radius of those areas such as Harambee or Halyard Park which is still slightly rough but competitively priced although rising....radius of Washington Heights (zip codes 53208 and 53210 are big duplex investor areas).

Obviously lots of research involving zoning, codes, and the rules in the area, but it can be done, and these types of properties usually cash flow well since they aren’t advertised as multiple units.