We are a growing family and need more space and of course, more opportunity for income building. 

thanks for your reply. that particular property is also a resale opportunity ..but I definitely need to know more about the how the system works. probably a trip tomorrow to the City of Chicago building department ..urghhhh

You could have the seller add you to title before the sale (you'd want an airtight contract), and then fund just the rehab in cash, sell the property and split the proceeds with the seller upon sale/exit. 

I'm not interested in seller financing as an alternative because I'm an introvert and not very good at sales.

If you sell, you'd just pay off whatever balance was owed at the time of the sale, the same way you would with conventional financing.If it cash flows for you while providing income for him, I think it's a win/win. 

Looking deeper..this will also have an impact on appraisals and lending practices as closed sales (similar to those with seller concessions) might not accurately reflect in a properties sales price. - Cash buyers could be big 'winner's' as generally there are fewer contingencies and theoretically could obtain a lower sales price and pay their representative directly. - First time home buyers (presumedly those that most intended to bring down 'affordability' could find less housing options)..why? 

@Justin BrownExploring off-market opportunities is a great strategy, and your friend's advice about searching for properties for rent on platforms like FB Marketplace and Craigslist can be a valuable approach.

We put the HELOC into foreclosure to avoid it getting wiped out in the sale (The senior would have survived the sale).

I know you want to buy another and start leveraging, but as long as you are paying less than you would for rent, save the difference and wait for an investment opportunity.

I'm getting good at sniffing them out thanks to these common red flags: they often have a foreign accent, they can't meet in person, they are looking for a quick cash sale so they're okay with me listing it below comps, don't want a "For Sale" sign placed at the property, etc.