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Microsoft cuts ties with the Surface Duo after just 2 Android version updates
(www.windowscentral.com)
This is a most excellent place for technology news and articles.
3 and 4 can be fixed with a portable USB DAC/AMP. Lots of options there.
Try going on a run with one of those. I have them too but they both have their places.
Plus in my experience, DAPs tend to be able to fit bigger amps in them than USB DACs which is good for driving less efficient headphones.