What information I should be analyzing to help me make a decision on where I should start.  

Best of luck with your decision!

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

@Chris Kay beleive you can do DSR loans without a job as they qualify the property, not the borrower.You'd still need 20-25% down though.That's where you have a decision:- Pay down the mortgage, setting yourself up for a future refinance to free up your VA Entitlement.OR- Save up for your next acquisition.Only YOU can make that decision as you have to be comfortable with the increasing debt-load risk and the additional time to manage everything.

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

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. 

.: Hello all,I’m looking for some advice on a real estate decision.

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.

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.

Was it the best financial decision ?