I think at least 100 years it could be enough time for the Canon Dovahkiin to die of Old age.
If it is set in a different province, why does it matter if the Dragonborn in Skyrim (the province) is still alive or not? As long as they keep details/rumors vague and ambiguous, it shouldn't matter, IMO.
The Nerevarine could have still been alive in the events of Oblivion, I think the developers handled it well enough.