Passive landlord is a long game enter anytime stay for decades and most will do just fine.Active engagement same thing enter anytime and your reward is how hard you work identifying the hot ticket at the time  access to capital etc etc..

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. 

Anybody know if Marquette, Michigan is going to lift their STR rental cap anytime soon? 

What I've thought of:-Offer to show my bank statements for up to 10 years showing I make enough money-If for any reason I cannot make my mortgage payments at anytime, I will agree to sign over the deed.I don't have any friends or family that would co sign, so I'm not sure what to do!

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.

@Hana Mori happy to connect any time your schedule permits!

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.