I'm ultimately just looking for some sort of advice; or maybe even just a nod of approval that I am on the "right" track.

I don't track Chicago area economics so I don't know what the driving force behind this sudden increase in migration is.  

So NO safety switch capability.

haha If you are going to do this, make sure you have a way of tracking it. 

How do they track how many rentals on the block or area?  

Quicken allows me to track each property, checking accounts and credit cards, property info like loan terms, available equity, etc., each tenant, lease info, store documents, and watch cash flow or P&L at a glance.  

You also want to review their plan and exit strategy and make sure they have a handle on the numbers and the market and have a good track record.

If you are going to do flips which many have said is not advised based on the assumption of a close by recession than you should be involved in the day work of a project manager including tracking the budget. 

You gain no economics of scale with onesie twosie deals that you constantly have to keep track of. 

This in my opinion makes it worth the cost above some of the others.One thing I have determined to really help keep me organized and on track is having everything I need in 1 app instead of multiple.