One thing that is black & white is that the manufacture and sale of Bootlegs is illegal.
They are counterfeit, pirate copies and they should neither be encouraged nor promoted.
That is the overriding principle as far as I'm concerned... and all the rest (its a rare scene, bollox) is propaganda.
As for the playing of Bootlegs at a local oldies night, I can see how it comes about and, lets face it, as many of the classics were done 30 odd years ago that particular genie is well out of the bottle and the damage, to lost sales, already done.
Certainly, 'vinyl' DJ's should always aim to play original vinyl. But those who play the occasional 30 odd year old pressing of a monster classic, to lift an oldies night, should probably not be hung for their actions.
That privilege should have been reserved for the bootleggers.
Sean