That is, @Bill B. is correct.While true that it’s harder to find P/HMLs willing to lend in second position than first, it’s also true that many of these will only lend behind a large conventional lender, such as a bank.

A business/way of life to continue? 

When people express concerns about starting an Airbnb in smaller markets, it genuinely amuses me, as this experience has proven that success is not limited by location.

Here is an update : https://chicagorealtor.com/advocacy/advocacy-resources/northwest-housing-preservation-ordinance-issue-summary/The DOH has posted the forms required to be in compliance with the ordinance which means any properties not under contract by 11/9 will need to be pulled off the market and 30-60 days notice must be provided before listing.  

Then, find 3-5 contractors to bid on your work, assuming you have a project to work on.

I plan to manage this property myself, manage the finances, manage the tenet forms and etc all by myself so I can learn how to do everything right away when I'm first starting.

Looking for some advice on how to structure my first partnership.

I would love to hear any advice or suggestions on how to proceed...We just closed on a place in Puerto Vallarta.

The best thing to do is to put each property in it's own LLC.

Quote from @Brendan Lawrence: Looking for solutions to offer financing to buyers:We have a unique asset class that we're building out here.