Apart from the spectator value of mounting a camera on one of the Starlink simulators, how much value would such a camera have to SpaceX in being able to monitor the re-entry? How long before the simulator was too far away / too hot to be able to continue transmitting useful images?

Ah yes, that would increase the separation quite quickly.
I guess they do the relight test after the simulator deploy because it is a higher risk activity - the pez dispenser is very unlikely to cause a RUD.