I agree with you about the phones to a large extent, although the quality bluetooth headphones are not the monsters they were 7-8 years ago; now you can get something that's light and flexible, and lasts for multiple days for normal use. BT pairing has also gotten a lot more reliable over that time, it's not something I really concern over any more.
For a laptop though, I think the days of headphone connectors are numbered. USB-c will be the defacto standard for all wired connections going forwards. Wireless connections for all peripherals, and eventually will gradually push out all wires into niche use cases. Something like the headphone jack, display port, HDMI, USB-A/B, TB2, and a variety of single/limited use ports will be caught between a hammer and anvil, and gradually fade into history.
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Nah, those don't seem to be very common usage cases. There isn't really much of any usage of headsets in an office setting except the situations I mentioned, mostly for voice/video conferencing.
I don't really see much of anyone taking out their laptop on a train just to listen to music, and I ride the subway just about every day; actually the last time I saw someone doing that is over a year ago. Taking a city bus using your laptop every day is asking for it to be damaged at some point in time. So unless you are talking about a relic like greyhounds, then there isn't much of a chance anyone does that on a regular basis.
Flying, true. But that is a tiny fraction of most people's lives, and a mobile device would be more than adequate if you are listening for entertainment. I have flown a dozen times or so in the last year, and using a laptop in a cramped economy class, with someone leaning back is hardly a comfortable experience if you are looking for in flight entertainment, even for a laptop as svelte as rMB. Almost everyone on the plane uses a laptop to get some work done, or in preparation for the meeting/conference they are flying to. For watching movies and shows, you are much better off packing a tablet or a large phone; or even buy a cheap tablet just for that purpose if you do this often enough.