International law firm ReedSmith weighs in on this point as well: '[O]nce the Department begins to audit and assess customers located within the city, many of those customers are likely to demand that providers collect the tax going forward. As a result, many providers will likely feel the need to register to collect the taxes, despite lacking nexus, and despite having strong arguments against the Department’s expansive interpretation of its taxing ordinances.'"
When the government starts auditing people and dunning for money, their first reaction is going to be, "how do I throw these clowns out of office?", they are not going to make a hue and cry and demand their service providers to collect taxes. These providers are also savvy, they will spend a little on lobbying, fund a few challengers and some incumbents
Knowing Chicago it looks more like another shakedown to get some campaign cash than to collect a new tax.