That's a valid point, brownie!
I am far too young to be in that same comfortable position, and the reissue practise of lots of labels is getting on my nerves (Columbia, Blue Note, Verve you name it). If they're only in it for the money, it's not too bad that others make some money, too.
Of course, as far as small labels doing good work with old recordings (such as the Uptown Mingus) - the 50 year thing is really problematic.
Now if there were clone labels really doing serious reissues, including complete sessions (unlike Proper, unlike Definitive), I would not hesitate too long and buy, but with things as they are now, I rather buy other music, on legitimate releases - which has the effect that my collection on pre-bebop music is pretty thin...
ubu