Those problems aren't really caused by Windows, so changing the OS probably doesn't solve much. Dongles and all that ilok crap is a main culprit and something to be avoided on DAWs.
OSX used to be superior for almost everything, much better than Windows, but it has since gone downhill while Windows has improved massively. I don't think switching now would be a significant overall improvement like it would have been 10 years ago, you'd just get different issues and different nuances.
OSX upgrades these days are a terrifying thing compared to Windows, their recent track record is laughable- unless you own a Mac. The hardware is still sexier and better built than typical PCs, the OS looks clean and has a real bash shell, but the price premium is a tad too steep for me to miss Mac anymore.
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