The ethics of free downloading

Humble apologies here at Caroline's place  but I do feel a rant (not a grnat!) coming on today.
Every so often you'll find on most forums a set of individuals posting a series of highly pious comments on a topic that has not one hint of grey between the black and white rigidity of their take.
Take downloading for instance.
No one can dispute if you take something currently available for free, you are depriving the owners -the record company- and artists money potentially although you may well recall taping your friends albums and if you liked it, then you'd buy your own copy in the days of lps and tape recorders.
But when it gets more complex is when a recording (or version) isn't actually available new because if you bought a used cd then the label and artist still are not getting anything  from the sale  and if you downloaded it for free at that level regardless of what the law may in certain territories say, it's the same outcome. The only person who makes any money from selling a used cd is the vendor.
What then if there is no cd out of a title but someone has 'digitized' the old tape or lp version that is out of print. Is there anything wrong with downloading that to listen on your iPod or replace a unavailable new damaged copy?
I wouldn't encourage people to download for free everything but the picture isn't so clear cut especially as many labels sit on catalogues that they show on balance sheets as assets and yet only issue a tiny fraction of them yet they will take  a person to court alleging they lost $***** amount of sales from it! If you have to download for free something, please consider attending a show or buying authorized merchandise so you share some love with your favourite musics creator.