Last time I was there it wasn't too hard. But it depends on if the Chinese government is blocking your VPN or not. I usually connected to Seoul or Hong Kong.
At the time no. But things have really changed. That said, my family lived through the Mao era and the Cultural Revolution, etc. Terrible things can happen but the rule of thumb for China, in my opinion, is that China (and probably any other authoritarian country) does not tolerate another nexus of power. Reading censor material is not so bad. Disseminating it will get you in trouble. Trying to speak out against the government and disseminate that opinion will get you disappeared. For example, Catholicism was banned in China for a long time until the Pope made a deal that gave the government a voice in the appointment of bishops. What made Catholicism problematic is that there is another authority figure in Rome. Buddhism, in the form commonly practiced in China, has no such figure which is why it was tolerated and sometimes even promoted (with a very nationalist slant). Tibetan Buddhism, on the other hand, has an authority figure not controlled by China. You get the idea...
It seems like it is a simple concept that you are getting at. Authoritarians want te prevent other seats of power. It makes me wonder about what the growing Chinese middle class wants.
EDIT: But back to the question. I think the answers make sense. It's easy to bypass if you are savvy (as we know already) but if you challenge govt they would take offense. I guess the grey area would be anonomous critique, but I digress; thanks for the response.
So your point about anonymous critique is somewhat true. It's actually a little more sophisticated than that. Critiques often come in the form of historical parallels. For example, rather than critiquing Xi for having a bunch of "yes" men, some high up official in the party lauded the achievements of Tang Taizong -- the second emperor of the Tang dynasty. He's generally considered an exemplary ruler but the other trait known about him is that he was open minded and sought out people who disagreed with him. China became very cosmopolitan under him and the silk road connected China to far away places (it's the inspiration for Xi's Belt and Road Initiative)
So in praising Tang Taizong, the official was critiquing Xi's inability to deal with differing opinions.
This isn't a new thing, BTW. Chinese scholar-officials have been doing this for ages. China has historically been a very authoritarian country and the same ideas applied then (kind of). This is one reason why historical Chinese officials were (ironically enough) criticized by the Communists for being backwards looking. Straight forward critique wasn't allowed during the imperial eras so they always had to find historical parallels to vail their critiques and advices.
No. Reading censored foreign media doesn't get you in trouble, and it's extremely widespread. Posting anti-government opinions is what gets you in trouble.
It is less about bypassing the censorship, more about what are you trying to do bypassing the censorship. I don't think you will have any problem reading stuff. Transferring information may cause you big trouble. As individual, I do not think you should worry about it at all.