Imagine a totally different scenario, where the government is about to cancel a defense acquisition program (like the F-22, which was cancelled). Could Lockheed-Martin bring this to the attention of the employees? If so, how?
I think the meat of the issue is that Uber doesn't get to decide Prop-22, it's a decision by California and if you want to sway CA talk to CA. If you legitimately think your business and all it gives to the economy and community would be destroyed by that proposition then tell that to all the residents of the state - targeted messaging to your employees is just all sorts of shady and, whether intended or not, it will leverage the power imbalance of the employer/employee relationship for some people.
It's pretty much the same reason you should look elsewhere for love - there is an existing relationship between an employer and employee - bringing other relationships into the scenario just makes things murky.
Large employers, with a lot of market power would still be able to communicate to their employees via public channels. Small employers with very little (employment) market power would be basically muted.
Is this what you're looking for?
If Uber just presented an explanation of the issues and allowed drivers to decide for themselves without any way for the platform to track their decision, no problem.
To seriously answer the question: I don't know where or how you'd draw the line in the sand.
There's a great Mitchell and Webb sketch about the issues with leaving things be implicitly communicated rather than explicit. (NSFW) https://www.youtube.com/watch?v=VgX6JFoV0TM
And, if I left out a clip of Always Sunny In Philadelphia's take of the pitfalls of implication, I'd be remiss. (NSFW) https://www.youtube.com/watch?v=-yUafzOXHPE