Nicely put Radrook. There is a physics point to this sort of discussion IMO, in that defining the likely life-span of Observers in cosmological terms tells us something about our present situation. Similarly discussions about the apparent "Cosmological Coincidence" that the mass-energy density and lambda/Dark-Energy are observed to be similar in size. In both "early" and "late" cosmological epochs this isn't necessarily so, which poses the conundrum as to why we observe the current near-unity of their ratio.
According to work by Greg Laughlin, Fred Adams and Peter Bodenheimer, stars should continue shining in the Galaxy at roughly the same observed level for the next ~trillion years. Low-mass stars, as they go off the Main Sequence, brighten significantly and experience a period of luminosity comparable to the Sun for ~5 billion years, enough time for Observers to evolve around any planets at ~Earth-like distances. As red-dwarfs are the most common stars in the Galaxy, then why don't we observe ourselves on one during its late-life blossoming? Why are we still in the "early days" of stellar evolution in orbit around a relatively high-mass star?
These are all valid questions, leading to fertile investigations in astrophysical processes, as evidence by the papers by Laughlin, Adams & Bodenheimer, for example. Late-time "speculation" is like any other astrophysical gedankenexperimenten
and thus well worthwhile.