I would recommend talking about these scenarios and laying out a plan to address them individually. 

I deal in distressed properties and I see deals sell in as little as 30 min to an hour on a daily basis. 

-How will you plan for the utility connections required for my project?

It's one of the lowest risk ways to get into RE investing and a great plan.

May plan is to pay cash and wait until interest rate improves, then refinance and pull out $150k for a down payment on a second property. 

See Nobel prize winner and associate  quote....Gunner Myrdal, an architect of Sweden’s welfare state who was given the Nobel Prize in economics as the left-wing balance to his co-winner FA Hayek:  Myrdal stated, “Rent control has in certain Western countries constituted, maybe, the worst example of poor planning by governments lacking courage and vision.”3 His fellow Swedish economist (and socialist) Assar Lindbeck asserted, “In many cases rent control appears to be the most efficient technique presently known to destroy a city—except for bombing.”Seattle is a prime example.

For each of the personas (enclosed), we have a different action plan. 

You think it will be passive because you are planning on hiring property managers, but that's a big cost for one property and you still have to manage the manager or your cash flow will dwindle.The way you are proposing what you want, you may get caught in a turnkey funnel and end up with less potential scale on the investment than you had hoped.

Plan is to purchase assets in the Louisville area to start but open to funding deals in other markets.

And the second duplex hasn't appreciated sufficiently to take advantage of the capital gains exemption yet, so planning to hold for the next few years.For this third duplex, however, I would like guidance on how to title it:1) Given that I am paying cash, and I am not totally sure I will sell this within the "2 years in the last 5 years" rule, should I just put it in a LLC rather than my personal name (thereby missing out on the gains exemption)?