Both practices are bad. Sharing passwords and weak passwords is doubly bad. Don't do that. A $47 billion company like WeWork should know better.
What exact alternative do you suggest? Having user-assigned password authentication through 802.1x, so that the company can track exactly how much WiFi each member uses, and at which hours? Thanks, but no thanks.
OTOH, installing their proprietary software for presentation/display access is an entirely different matter, and that one is, indeed, a complete dealbreaker for me, security-wise; I don't understand why anyone would want to do that; just as I don't understand why you'd rather them secure the WiFi for you, instead of doing your own VPN as you see fit.
I am not aware of any issues using a VPN at WeWork; it works great; I'm sure lots of businesses use it, too. It especially works great because there are no stupid captive or landing pages like you get at so many other places, and the password just works, too.