I think the decision to seek cash flow over appreciation can be misguided because the best looking cash flow won't stay that way.

Here's a link to the data: https://mred.stats.10kresearch.com/infoserv/s-v1/vwxv-Zs5What this data shows at a Macro level is that the Chicago market is doing fine, but the market is too large to use that data to make any decisions about where you want to house hack.

I want to make the best decision while honoring my agreements and maintaining professional integrity in this deal.

Was it the best financial decision ?

Well worth the money, plus you will have already factored that expense in to your cash-on-cash requirements to justify a purchase decision)4. 

It’s true that while the 10% down payment for a second home sounds appealing, the fact that rate adjustments are now similar makes the distinction less about cost and more about strategy.A few years ago, I helped a couple in San Diego navigate this exact decision.

Anyway, we've made a decision, based on all the advice and knowledge from everyone here, to continue to look for a real buyer. 

As long as you are comfortable with the sponsor (Brian has a solid reputation) and the opportunity meets your criteria, then it is your decision to move forward with the investment.

You want an accountant who can help you strategize and who is responsive when you want to know the consequences of the financial decisions you are making throughout the year.Good luck.

I don't think I can see and downside to this decision.2.