Jordan, Across MN in the heavy tourism areas, STR PM's are very common.

As Sean Wagner mentioned, the city of Chicago has adopted their own regulations on charging what's commonly referred to as a "security deposit" you need to do it another way. 

Sewer issues in Chicago are very common which is why I ALWAYS recommend / almost require my clients to get them done + if there's trees in front or in the back of a property, there will almost always be plumbing issues + needed rodding. 

Cash for keys is common, and frequently the part that keeps tenants from moving forward is not having an affordable place to go to.

I think development is getting more and more common since we're so undersupplied in housing. 

Yes it’s common to have an additional guarantor who has a balance sheet added as a credit enhancement.

These programs very commonly involve restrictions and conditions on use, refinance, or resale of the property. 

My advice is good advice, but it's common that most people new to wholesaling still think they are going to make a mil in a year and only want to hear the good stuff.

Each bedroom shouldn't need to go through the common area to exit the building4.

When adversity arises, its very easy to shut down, stop communicating and toss around legal threats.