Hello John,
If the waking up part is the only problem, there is an easy fix for it without even getting any new watches involved. I know this is a watch forum and you'd probably want to get some watch suggestions.
But to solve the whole thing on a solution based approach:
Just tell him to set an alarm on his phone, make sure the vibra is set on and put it in his pants' front bag.
I rarely ever travel by train but if I do so, I always have headphones or earplugs on. And I almost always fall asleep after just a few minutes. So to make sure I don't fall asleep and miss my exit, I just set an alarm with vibra and put my phone in my pants' front bag. I can assure you that it works, and on the modern smartphones you can even set up a vibra-only alarm.
. That way, nobody else gets "molested"
Hope that helps,
Best, Stephan
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