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But this seems to be OP's point: he didn't think he was taking on the West. He thought (very reasonably) that he was taking on a demoralised meme country ruled by kleptocrats with a giant Russian fifth column. I concur that the smart bet in Feb was that Ukraine would fall like a house of cards while it's elites flee to a cushy Swiss government in exile. The country wasn't swimming in Western materiél back then; if the three day blitzkrieg had worked, there would have been no taking on of the west at all because the special military operation would have been a fait accompli before the Javelins arrived in numbers. That it has now morphed into such a take-on-the-west conflict was probably unexpected by Putin (and, indeed, everyone).
While I can't claim to have had the foresight to predict that actually Ukraine would put up ferocious resistance, I'd argue in retrospect it shouldn't have been that surprising - the Ukrainians had popular uprisings that threw out pro-Russian political leadership in 2004 and 2014, then fought an 8 year war against Russian invasion (albeit on heavily constrained terms). While breaking with Russia was internally contentious, it should have been clear that on the whole that Ukraine had the will to fight. Why we all ignored that, I'm not sure, other than everyone agreed that Ukraine was a joke of a country and Russia was a "near-peer" military of the United States.
"Popular uprisings" don't usually result in one's cabinet being full of foreigners hand-picked by the American state department, so suffice to say that my read of the events of 2014 don't predict popular support for the Euromaidan regime.
If course this then requires me to explain 2022, but like OP I'm going to opt for a verdict of "idiopathic, was more likely to go the other way". With maybe a side order that the American state department employees are more invested in Russiphobia than Talibanophobia, so their fingers were more firmly holding the puppet strings on Zelinsky than they were on Ghani.
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I think of this interview when I think of Putin's decision:
"... if you really look at the total message the US was projecting to Russia in those critical months, there were two messages. One is, 'We’ve got great intelligence on you. We actually understand you much better than you think.' It was shocking. I think it shocked the Russians. But on the other hand, we’re saying, 'We think you’re going to win quickly in Ukraine. We’re offering Zelenskyy a plane ride out of Kyiv. We’re pulling out all our diplomats and urging other countries to pull out their diplomats.'
The message, actually the totality of the message that we sent to Putin is, 'You are going to win if you do this.' "
https://conversationswithtyler.com/episodes/walter-russell-mead/
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No one fought him when he took over Crimea. Not the Crimeans, not the other Ukrainians, not Washington or Brussels either. The Crimeans seemed to be fine with it. In the Donbass he got more resistance, but still not a lot. (Of course, this was all just after a Western-backed coup that was unpopular in the south and east.)
He clearly thought he could do the same to all Ukraine. He was wrong, but you can see how such an error might be made.
There absolutely was a lot of resistance in Donbass, even before it turned into combat between armies/militias. There were plenty of anti-Maidan-turned-pro-separatist attempts at finding new "People's Republics" or expanding the borders of ones that got off that failed due to resistance, if the separatists could have done it they would have gladly seized many of the currently occupied territories in 2014.
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My guess as to how it would turn out when the invasion started was that Russians would quickly take over large parts of the country, larger than they did, and hold them at least for a while, but that there would also be a fierce guerrilla war leading to much difficulty for them. That there were a shitload of people in Ukraine willing to fight fiercely was never in doubt for me, what was surprising that this fighting would happen in a conventional way and not through partisan attacks.
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