That's great, but what are you going to do about the larger problem of a declining local tax base?
Fewer Chicagoans, apparently, are employed in building network infrastructure and data centers than in things like video rental and so on, and the more people who are happy to use Netflix the more money flows out of Chicago's local economy. Meanwhile the cost of providing services within the city presumably remains about the same. I gather Chicago has massive unfunded pension obligations due to union lobbying and so forth, but for all practical purposes those are like any other unwanted financial obligation, they're not going away unless you can come up with a good reason why those secured creditors should give up the property interest they negotiated.
several hundred companies that are all going to have to implement this tax in their software if they want to sell locally
Well, this isn't very logical. First, there are 3 million people in Chicago which is a significant market, so it's very unlikely that any firm is going to suddenly refuse to do business with anyone in Cook County even though the administrative cost of said business is due to rise. Where a business is located is wholly irrelevant in this case because it's a consumption tax, so how is it going to kill any jobs in Chicago?
Also, why would you expect these companies to implement the tax in their software? That would be absurd. There are lots of software-as-a-service companies that take care of calculating sales taxes and suchlike so that other companies don't have to, just as there are companies that specialize in administering payroll or other business tasks so that firms can focus on their core competency. From a startup's point of view the additional administrative overhead is likely to be marginal.
We're going to kill this thing.
Oh stop. It's easy to stand up and say you're going to be against some unpopular measure, but that doesn't address the deeper problem. What is your better alternative solution? Forgive me for touching on national politics, but I'm reminded of the national Republican effort to kill Obamacare; I understand what your party dislikes about it, but after 50+ votes to repeal it and endless speechifying there's no results and no concrete alternative on the table. The repeal argument depends on a nostalgic argument that everything was working great before the unwanted policy came along, but the reality is that the previous systems were deeply unpopular and dysfunctional.
It's not that you shouldn't be against this proposal, I share your belief that casting around for new things to slap taxes on is a bad way to shore up public finances. But your arguments are shallow and being against things isn't a real economic program. What positive proposals do you have?