I agree, but Vail is not involved.

I was hoping to structure a deal that involves paying the seller every month and then a balloon payment in 5 years (when I can get an 80% LTV cash out refinance to put a mortgage on the property without having to put any money down because I'll have built up at least 20%).

When you surround yourself with a great team, are well-educated, and use data to make your decisions, your odds of a significant issue are VERY LOW.Continue to network with the awesome community here in Chicago, and you will stay on the right path.

Quote from @AJ WongWong: HI James, coincidentally just wrapped a convo with a community member about the exact strategy (and oddly location!).

It just doesn't strike me as that odd or out of pocket that an older, single mother of a disabled son can't afford 1500$ in rent.

You might feel like the effort doesn't justify the cost, but she was involved on the initial showing and that's what demonstrates the agency between you two. 

A hybrid approach involves buying early and renting out units, then moving into one.

So yes, to answer your question, I’m well prepared for whatever I get myself involved in.

When making offer based on ARV, is it good practice to have future cash refi lender get involved as early as possible (have their appraiser connected?)

That definitely helps explain things, but too messy for me to get involved personally.