The other thing is what @Joe Villeneuve mentioned above: how can you parlay living costs into the equation so that a deal makes sense?

So your goal is to invest in appreciating assets to parlay in depreciating liabilities? 

I highly doubt they informed the seller that they have no money..in fact, I would wager they don't operate in that manner.

I love real estate, and I love hosting, and am keen on making some connections on BP to help take the next step into my next property.Beyond being a hobby, Airbnb has so thoroughly juiced the returns on my condo (appx 2.5X long-term) that it only makes sense to try and parlay this strategy into a bigger and better play.  

Rents are comparable in both markets, but I would wager Kenosha will see greater appreciation over the long-term based on the gentrification from IL and surrounding areas.

It varies, if the markets hot I'll sell and parlay that money into more investments in the local currency.  

@David White never done it but if we are talking big deals with large unit counts I would invest in a syndicated deal or two or three that includes the opportunity to learn so you can get education and experience that could then be parlayed into your own deals.

Most of the multi-unit groups I'm familiar with, typically recommend that you start building your SFH portfolio until you get about 5 up and running and then at the right time parlay that into a multi-unit property. 

You're doing this (I assume) to parlay all that money you save (or earn on top of PITI/Expenses/Capex) into your next real estate deal, so treat it like you aren't living there.

If you can find them, you can find a funder interested in those notes, earning fees that way, thereby amassing capital with which to eventually buy your own notes to hold or resell or parlay into other assets.