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.

I think the outskirts are you best bets!

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

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. 

i think the gift basket may be more beneficial to real estate agents to get referrals and possibly to get new tenants. i bet that was nice, i wouldn't forget that either!

You bet.

And yet I would bet that any property that's not brand new or fairly new, will have some items that could fall into this category.

So starting with an agent probably won't work.Your best bet is to start networking, going to meetups, etc.