I agree with the idea that HK was an experiment by China to see what could be gained under a western democratic model.
West was painted into a corner with HK. Thatcher tried her best to hang onto HK, proposing all kinds of left-field ideas like "sharing" HK or making another 99-year lease. These were obviously all rejected. If they didn't handover HK, then basically it proved that they were looking to continue the exploitative colonial economic model. Furthermore, this risked fighting a war, which despite an overwhelming technological advantage at the time, it would be far riskier than something like the contemporary Desert Storm. So as you mention, the best they could do was hand back HK and hopefully HK could act like a Trojan Horse. As you mention, adopting the western model is not simply a matter of "electing government", but rather a general subservience to American interests in exchange for "a cut of the pie".
After the fall of the Soviet Union, there was an overwhelming idea amongst Western intellectuals that the western liberalism "had won". This was popularized by Francis Fukuyama's "The End of History". The fall of the Chinese Communist Party would be inevitable, especially with Tiananmen fresh in people's memory. The entry into WTO would accelerate the decline as it was believed that the government and state-owned industries would not be nimble enough to adapt and compete to the opening up. To be fair, they had plenty of reasons to believe this, productivity, mechanization, technological sophistication were all very low. How could China catch up being so far behind? See Jim Mann's book "Beijing Jeep" to illustrate how most American business people saw China.
So with this backdrop, basically for 20 years, HK was left alone by the Chinese central government and was not an issue for Western governments. There was a still a belief that Russia's struggles adapting to the new global economy would soon play out in China. However, basically when Obama took power, it was increasingly obvious that the system in China was adapting and actually thriving. The country had managed to turn the tide on exploitative manufacturing and was able to innovate in fields like high speed rail. High speed rail would be less polluting (especially with the move away from coal), less dependent on foreign imports (both technological and oil), and cheaper to run per capita. The main downside being slower, but when looking at total travel time (including time to get to the airport and crossing security), you are only losing an hour or 2 for plane trips under 6 hours. Although high speed rail in itself is not anything super special, at this time, Boeing was growing fat and rich from Chinese airline purchases, and by association GE. It was a real wake up call that China was moving forward on its own terms. So you also see very quickly that the western machinery was mobilized against the HSR system at this time. 2011 was the Wenzhou train crash, and all media cried out about officials covering up safety defects, the downfalls of intellectual property theft, etc. etc. The reality is that at some point an accident is inevitable, that is the sad truth.
What is the point of talking about HSR? HSR is the road that leads into the rise of western interference in HK. The timing of the Wenzhou train accident was seen as very fortuitous for western strategists. They seized on the timing as construction had only just started at the time. They quickly mobilized their army of "enlightened intellectuals". According to Joshua Wong himself, this was his first protest. So we can see the younger generation cutting their teeth for their benefactors here. From the safety issues, then they moved onto sovereignty issues. They made a big deal about mainland officers stationed there to do customs clearance. In actuality, this is a very standard practice by the USA itself.
However, I don't think that independence was a serious end goal. The main goal here is to maintain the divide between HK and mainland. The next step was fomenting the Umbrella and Occupy protests and solidifying the newly installed opposition players (Martin Lee and Jimmy Lai were already old). The same thing happened in Taiwan with much greater success for American interests. Ma Yingjeou was about to cap off his presidency with the Free Trade agreement with mainland when it was derailed by the contemporaneous Sunflower protests. Very quickly American interests moved to destroy relations with the mainland which had been on the rise.
These are the hallmarks of typical backhanded American geopolitical moves. First the problem is created by them, then they criticize the affected country for "silencing the opposition" or whatever nonsense. This exact playbook was also seen in Ukraine where US agitation forced a coup, then blamed Russia for destabilizing the region and intimidating Ukraine.
Broadly agree with most of what you said, expect for a few key points.
Firstly, I think that western malevolent forces were busy at work to create their Fifth Column foot soldiers long before 2011. Basically it started as soon as the British agreed to hand back HK.
On top the the obvious money grab projects that everyone noticed, there were a lot of other moves, most of which were not noticed or picked up.
You have effective sleeper cells who moved into key areas like education, judiciary, media and the like and started to promote anti-Chinese views.
Vietnamese Wong might have went to his first protest in 2011, but the teachers that radicalised him would have been radicalised themselves a whole generation before from those first seeder cells. After which it grew exponentially with each generation.
These forces were not created for any specific operation, but rather were to artificially create an entirely new segment of society (as evidenced by the fact that the most virulently anti-Chinese condoms were all born after handover) who’s sole distinguishing feature is a general western worship and anti-China world view.
They could be relied upon as an election base to form a political party to try to paralysis HK government while they are in opposition and try to use that to generate popular support for ‘reform’, as a pretext to seize power and basically do the west’s bidding and maintain their interests in HK.
This was a long conn and is still generations away from reaching their ultimate goal, but was already starting to bear bitter fruit for China.
Trump fucked it all up because he wanted bargaining chips to win his trade war with China, and ordered the CIA to go the colour revolution route instead to produce immediate results that he could try and leverage.
Best case scenario for Trump was that he snap his fingers and HK descents into chaos and it panics Beijing so much (remember all the ridiculous western MSM early editorials suggesting how mainland cities would rise up in support of HK?) that they basically cave to Trump’s fantastical trade demands so Trump would snap all the cockroaches back into their holes once more.
The fall back was that Beijing panics and overreacts and send in the troops to butcher all the condoms in live TV and gives Trump enough leverage to force the EU into effectively joining his trade war against China by imposing massive and sweeping sanctions on all trade with China.
Problem for Trump was that China’s leaders were a lot more mature and capable than he bargained for, and they managed to end the chaos with no loss of life and minimal use of police force.
The crowing irony was that it wasn’t mainland Chinese cities that rose up in revolt following HK’s lead, but instead American cities started to burn as BLM arose, much to the consternation of Trump and the condoms rioting in HK, because they are overwhelmingly white-worshipping, self-hating racists at heart and just absolutely detested being compared to and lumped together with the ‘inferior blacks’.
