After reading the Black swan (Taken), I stopped reading every news outlet and did my best to not know up to the minute news. Like the author, I've felt more informed and able to make better decisions and hold better conversations because I'm not bombarded by constantly changing "facts". In fact, I feel liberated and but inundated with microscopic thoughts, but instead more general ideas. YMMV.
We're also in Chicago, have seen tons of space like WeWork, and decided for the pet person cost it was more effective to get a commercial lease. Yes it was unnerving to sign a 3 year lease (especially as a boot strapped startup), but we just renewed for our 4th year!
As for Co working spaces, I think they have a place, but once you hit 1 or 2 other coworkers, you need your own space. It's worth the lawyer for reviewing what you're getting in to, but I do agree, there's a lot of sketchy places with dodgy and gross problems. But you can find nice spots if you're patient and diligent.
In Chicago there's a robot store always looking for teachers to help students about that age range (maybe even younger). Can't remember details, but if your city has a robotics store, chances are they can help you get into teaching.