The regulations in Chicago can be quite overwhelming, so I’m looking forward to exploring the opportunities in this area. 

@Joel Wilmoth is a local PM   And and there are others just look through all these threads there are 3 or 4 that have taken an interest and will help.. also if you really think you have been wronged here and its your lifesavings you certainly should let the state of Indiana regulators know what's up its free. 

Be aware of any local regulations in Emeryville as well.Please make sure your 4plex isn't exempt from AB 1482.

Use some for buy and hold (I personally would prefer apartments rather than buying a few single family homes) and some for lending/trust deed investing.In either category, you must know what you are doing, know how to vet the investment, how to vet the sponsor (if investing in a larger fund of some sort), the laws and regulations on the lending side, how to investigate which areas to invest in buy and hold and notes/trust deeds for that matter.So as you have already said several times, lots to think about . . . 

Your definition is correct for "legal non-conforming".The "legal" part of "non-conforming" is dropped when it doesn't apply so most commonly people call these units "non-conforming", "finished", "in-law suite/unit", or "bonus unit".Non-conforming: Any property that doesn't meet current zoning requirements.Legal non-conforming: A non-conforming property that was lawfully established under previous zoning regulations and is allowed to continue its use.Based on his posts @Mario Morales is referring to a non-conforming unit.

We will continue to have an influx of transplants from high tax, high regulation states like CA and NY. 

When I appraised notes for the State of Missouri, the very first question I had was "Is this obligation enforceable, was it in compliance with rules, regulations and laws at the time it was originated?

There's a to unpack here - preparing the property, pictures & listing, finding a management company, taxes, regulations for the area etc.

Navigating NYC's zoning regulations can be complex @Jon Pflueger, especially in M1-2 districts, which are primarily designated for light manufacturing and commercial uses.

There will always be bad actors, you will never regulate malintent away.