My questions are what books or other resources would you recommend to someone just getting started and also what is the best path to get started on in real estate for someone in my position?

On the positive side, it seems like you have a good potential BRRRR that you can use to purchase additional properties.

Agents here in our Metro Detroit market would be insulted by such a low amount and would bad-mouth us to no end.Guessing flat rate Placement Fee means only advertised on PMC website and the Zillow triad?

The positive is you can get them out with 60 day notice so 60 day escrow would allow the unit to be delivered vacant (assuming zero issues terminating the rental)good luck 

The Suburban markets with New construction offering decent builder buy-down rates 5s %, and selling completed inventory homes to investors is an opportunity we’re pointing investors to, as well as Duplexes outside the city, that’s where we’re finding some of the best options to get closest to positive cashflow with 20/25% down.

-- How many and which websites is it on overall?

Pretty much any regular bank / lender is going to require themselves to be in first position on all the properties... so I don't think a HELOC type solution is going to work across multiple properties with multiple lenders.  

I have a list of them that I can share with you.Chicago, without a doubt, has some downsides, but there are also a lot of positives, like the inventory of older multi-family properties and price points at all levels.Investing out-state can be challenging because of the distance and the need for boots on the ground that you can trust 100%.

@Connor O'Brien CHA does release payment standards that can be found on their website but those are maximums, not guaranteed. 

You’re in a great position with a property that’s appreciated significantly, a low-interest mortgage, and clear goals to boost cash flow and transition into full-time investing.