I would have expected that the EOTD needs to by in some way or the other "synced" with the HOTD in the loco and so the freight conductor (or whoever is in charge of this stuff) would replace it when the leading loco is changed. But I have no idea.
Generally speaking, any EOT works with any loco regardless of RR, they all use the same radio frequency and data language. There is a unique number code that is synced to the head end, nothing to do with railroad specific programming. Not uncommon to have them stray off property especially on through trains that don’t get broken up with run through power. They eventually make their way home...
Yup. And I’ve seen before EOTs with old UPS shipping labels on them addressed back to their home. Sooner or later they find their way back.
I think this is just an oversight by the freight car substitution system for Oakville, since whatever car at the end will have the EOTD that is from its home route, not the one from OSD
Things from other networks will frequently find themselves on others, even things like wagons I believe. In fact in the UK the Class 166s and 165s were purposely made to be incompatible with 14x and 15x units despite having the same coupler solely to stop the trains being 'stolen' from their home routes and used by Regional Railways.