Overall, it looks like part of the reason it worked so long is because they didn't have any major disasters to really shake up their ideology and sense of comfort: smaller conflicts, maybe, but not big ones. All it took was a major war, and the Jedi started to splinter within a few years despite those hundreds of years of history.
Over the course of the Clone Wars, no less than five Jedi or Jedi apprentices fell to the Dark Side (probably more, if my count isn't right) - some extremely powerful. Even Sifo Dias, who didn't turn, still went out and commissioned an army based on paranoia and dissatisfaction with the Council's complacency.
Even if Sidious hadn't recruited Anakin, there's a good case to be made that the Order would never have been the same again.
edited 1st Apr '18 10:19:24 AM by KnownUnknown
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That-although that raises a question. Because of when precisely the commission was taken, it means that Dooku had already fallen by the start of TPM; Sifo Dyas was killed after ordering the army, but before TPM because he was redirected while on a mission for Valorum while Valorum was still Chancellor, resulting in his death at the hand of Dooku. The order had to be placed before then, but Valorum was removed from office during TPM.
That means Dooku had already been corrupted and recruited by Sidious before TPM starts, and Maul was still kicking-creating the implication that Sidious had already decided to replace Maul with a more worthy/useful apprentice, even before coming into contact with Anakin. That puts an entirely different complexion on Sidious' various plans.
edited 1st Apr '18 2:39:35 PM by ViperMagnum357
It's been said that Maul was acquired and trained under both Plagueis and Sidious in defiance of the rule of two and as such never intended as a true apprentice to take over the master. Plagueis himself was still alive at the start of the TPM and Palpatine killed him the very day he became Chancellor (all the news about the new Chancellor and the battle of Naboo overshadowed the news of Plagueis's death in his civilian identity), meaning depending on the timing he may have even outlived Maul's apparent death.
Also, when someone says "ten years ago" it can mean a large buffer, usually give or take 6 months. Meaning two events "ten years ago" could have actually been about a year apart. I believe it was said that Dooku left the Order before TPM, but it could have been several months afterwards that he was turned by Palpative and proceeded to hijack Sifo Dyas' plan and kill him.
For me personally, I prefer the idea of villains co-opting unforeseen events and integrating them into a larger scheme rather than having everything planned out in advance. It makes the villain feel clever rather than the plot bend to their will. So I'd prefer that Dooku was converted after the death of Maul. Functionally there is no real reason to have specifically a Sith Apprentice be the leader of the Separatists, as it could have been any charismatic figure under Sidious' influence.
That the old Order was flawed is clear. It was outright spelled out in the novelization of Rot S. Yoda had an entire inner monologue during his fight with Palpatine in which he acknowledged that he had lost even before his lightsaber clashed with Palpatine's. The Old Jedi Order had grown complacent after their apparent victory over the old Sith. Yoda realized that the Sith had not remained complacent. They changed, they evolved, they became politicians. The Old Jedi had prepared themselves to fight the same war, but the Sith made war itself their weapon. The Jedi lost the moment they entered the war.
The novelization also gives this as the explanation for why Luke and Leia were not trained by Yoda and Obiwan from the start. Obiwan wanted to do it, but Yoda believed that the old Order's failure was proof that their ways were flawed. He believed that the twins needed to go down their own paths in life.
edited 1st Apr '18 11:52:33 PM by M84
Disgusted, but not surprisedI mean, I guess you could argue that the Jedi weren't proactive enough when it came to reforming the republic - but should they really be held responsible for not clearing up every mess in the galaxy? It would be very easy for them to become tyrants.
Palpatine's rise came about because of political weakness in the Republic - he could have probably carried out his master plan without being a Sith actually. I think the vast majority of blame should fall on the political classes at the time, not the Jedi.
"And when the last law was down and the Devil turned round on you, where would you hide, the laws all being flat?"Palpatine used The Dreaded reputation of the Sith to cow people like the Trade Federation into engineering crises which helped his political career. It's true he never really seemed to use actual Force powers to achieve his ends.
The Old Jedi Order were ultimately blindsided since they never expected the Sith to (temporarily) retire the Evil Sorcerer shtick for politics.
edited 2nd Apr '18 12:08:18 PM by M84
Disgusted, but not surprisedThe problem is that the Jedi became too intertwined with the Republic. In the old EU after Ruusaan they were brought under the jurisdiction of the Judicial Forces because the Republic didn't like another powerful group of Force-users having armies, planets, and fleets that weren't under its control.
Mark Hamill had a very interesting idea
for where he'd take Luke's story if it was all up to him. He'd actually have him renounce Jedi-hood too... for love.

The old rules worked in the sense of preventing more Vader’s, until the one time they bent them to allow Anakin in.
The old rules did not work when it came to the Jedi being unable to find Sidious, and without Anakin he could’ve easily reached his rise to power still with many other apprentice candidates.