I'm betting your numbers look like mine, and CapEx saving is eating up a lot of it.

Doing this like a brrrr I see as the best bet, for example my property does still have room for improvement adding a bedroom and bath to the primary structure and then the ADU.

The safest bet is to try to get a variance from Union City. though clever, your combined unit lease agreement would likely cause trouble if ever scrutinized by the Tenants or the municipality. 

And that gave us a feeling of security that allowed us to take "riskier" bets.

As you concede, you and your tenant buyers made opposite bets on appreciation over the 3 year period in setting the option price. 

I think the outskirts are you best bets!

To avoid partnership issues, 50/50 is likely your best bet.

@Guillermo Nadal I would say its premature to put this one in the win column wouldn't you say? 

She's an agent that works in that area and does a ton of work with out-of-state investors.I think NW Indiana is a great bet, it provides solid cash flow and continues to have Chicagoans flood that way to avoid taxes. 

On my county's website there's a legal description on the right column, that should lead me to the records that have RE?!?!?