I'm thinking of solar neutrinos which, for a while, we weren't sure if they were massless or not. We had to observe them experiencing a duration of time to conclude they were massive. If we didn't find that, maybe it was just an even shorter duration, not the absence of one and we would never be able to tell the difference.
Are you asking if there is a way to distinguish a timelike object from a lightlike object? Of course there is. The fact that, for something that has a very, very small invariant mass, it might be practically difficult does not change the fundamental principle.
Also note that the reason it was difficult, for example, to tell whether neutrinos have mass or not is that we can't just do the obvious and straightforward thing and find an inertial frame in which they are at rest (by, for example, taking a rocket and accelerating it in the direction of a neutrino to see if we can bring it to rest relative to the rocket). So we have to resort to indirect methods. But, again, that's a practical limitation that doesn't change the fundamental principle.
For neutrinos, even if we accelerated an rocket and somehow checked if a neutrino was at rest relative to it, we might find that it's not. That means we won't know if we need more speed or if it's impossible. I suppose it's a bit easier than that because we only have to accelerate the rocket fast enough that the neutrino's speed becomes measurably less than c, rather than 0. But still, what if we can't even get it to go fast enough for that? No way to prove that it's travelling at c, it seems.
I'd like to add that even photons have a nonzero upper bound to their possible rest mass. At least they used to. Is there any way, in principle, to show that it's exactly zero, and thus falls into this distinct category?
If you try what I described with a light ray, it will be moving away from you at c no matter how much you accelerate in its direction.
If you try it with a massive object, even a neutrino with a very, very tiny invariant mass, that will not be the case; its speed relative to you will decrease as you accelerate after it, eventually to zero.
There is no continuum between those two possibilities; they are distinct and discrete. The only continuum is in the latter case, where the final speed of the object relative to you will depend continuously on how long you accelerate.
> even if we accelerated an rocket and somehow checked if a neutrino was at rest relative to it, we might find that it's not. That means we won't know if we need more speed or if it's impossible
Yes, you will know, because you will know if the neutrino's speed relative to you has decreased or not. If it has, it's possible to bring it to rest relative to you. If it hasn't, it's not. See above.
> I suppose it's a bit easier than that because we only have to accelerate the rocket fast enough that the neutrino's speed becomes measurably less than c, rather than 0.
Exactly.
> But still, what if we can't even get it to go fast enough for that?
That's basically the position we are in now: we have no way of building a rocket or other device that can accelerate after a neutrino long enough to tell whether its speed relative to the rocket is measurably decreasing. So we have to resort to indirect measurements. But as I said before, that doesn't change the principle.
> even photons have a nonzero upper bound to their possible rest mass
Yes, because, as I said, practically speaking we can't run the obvious and straightforward experiment I described, to confirm that a photon moves away from you at c no matter how much you accelerate after it. So we have to resort to indirect measurements, like trying to measure its invariant mass by other means. But that doesn't change the principle.
> I'd like to add that even photons have a nonzero upper bound to their possible rest mass. At least they used to. Not sure what you're talking about, their momentum? No object with mass can reach the speed of light and we know they're travelling at that exact speed.
