Yes, it is hard to win peacefully against a dictatorship, but I don't think the chance of winning via violence is high either. I am kind of gave up at that point, not hoping for something better, just wish that the situation would not worsen too much.
To be honest, I think technology is increasing the power imbalance between the public and the ruler. We have AI for surveillance system that can track the activity of every single citizen. The media and social media can overload most of the people with useless information, distracting them from the important issues. Advanced weapons so people have no chance in winning the fight if the authority don't care about casualties.
I also lived in Hongkong during the last rounds of protests. One of the comments I frequently heard from foreigners from stable, highly-functioning democracies: "I cannot condone (support) violence during political protests." On the surface, it sounds great -- very pithy (short, succint)! Then, I thought a long time about it. Peaceful protests mostly do not work in non-democracies (dictatorships). For me, this is the reason why transition to democracy in Taiwan, (South) Korea, and Indonesia was so violent. (OMG: Go and read about Korea. It reads like a civil war. Protesters stole automatic weapons from police stations to used against the police. It was crazy!)
If readers are unfamiliar with the transition to democracy for these three countries, or the current state of affairs, I strongly recommend a "rabbit hole" deep-dive on Wiki. You will be impressed! And when you observe these three democracies from afar, you will be further impressed by their passion to create a great society that is governed by the people. People in their 50s sound like high school students from highly functioning democracies when they discuss government affairs. It is very inspiring!
A different angle: When you live in a highly functioning democracy, protests of any size always capture the attentions of politicians (members of parliment, etc.). Why? Because they represent the people, and they can lose the next election if they do not listen. In low functioning/non-democracies, protests can be ignored and protesters arrested / beaten / gassed. Why? Because accountability is so low.
I will never forget walking through a Hongkong wet market to buy groceries (veg, fish, etc.) and being tear-gassed by the HK riot police. Yes, I regularly attended protests, but on that day, I was simply shopping for a weekend meal. Their annoucements were only in Cantonese. The domestic helpers (Indos and Fils) in the market were terrified. It was an all-out assault on humanity. I sent careful documentation of the event and evidence to the police, but my complaint was entirely ignored. I knew this would happen, but still, I filed my complaint.
At the peak of the 2019 protests, there were unjustified, daily beatings by police of protesters. An unimaginable amount of mobile phone video footage was captured, but not a single HK police officer ever faced the court system for their appalling behaviour. They was an incident on the HK metro where police officers boarded a train to confront protesters peacefully delaying service. It was a particularly grotest display of police brutality. They swung metal batons at unarmed civilians causing so much harm. (These YouTube videos were later used in Taiwan election adverts!) It does not mean that every protester was innocent, but you will never win peacefully against a dictatorship. Sadly, violence is required. (See Burma / Myanmar!)
At some point, HK gov't pledged to create an international council to help them decide how to handle arrests on both sides. Once the foreigners selected saw the total lack of accountability, 100% of them resigned from the board. It was a collassal embarassment to the still paper-thin democratic system in HK.