A lot of what you say describes a fairly common experience with Windows too. Perhaps not with a Thinkpad maybe but I’ve failed to revive a sleeping windows machine on a few occasions, and switching between output sources can be unpredictable too. Mac is the only platform which consistenly succeeds at these kinds of things because of the vertically integrates hardware. Its the drivers as you say ... I don’t think the actual o/s has much say in it beyond the drivers that are supported.
A mix of dock and undock with multiple monitors is dodgy; like rolling a die. Plugging in the display port cable after a resume from a prior docked suspend, for a presentation, is flipping a coin.