STR Arbitrage & SHOUL - Question for any successful operators

[Eric Lee]

Hello BP crew,

I am seeking advice from any successful arbitragers operating in the City of Chicago, with more than 1 property & a Shared Housing Operator's License. 

I know the City has made it difficult to operate more than one, but I can see other hosts with multiple short term listings, so I know it must be possible? I have operated an STR out of my primary residence for almost a year. From my understanding, that leaves apartment buildings with 5+ units as my only option.

My main questions are:  Are you pitching the landlord first, and then applying for the BACP registration number?  

When applying for the registration, which option is correct for your "relationship to the property"?  Both options seem technically correct to me: "I manage this property on behalf of the owner" vs "I rent / lease the property".  

Any advice from successful arbitragers with multiple registration numbers would be greatly appreciated!