I just ALWAYS use the 'increment file name' option when I'm rendering. I render straight to "Music" in my Home folder--however, comma, my actual music libraries are stored on a separate hard drive, so this folder is otherwise empty. It only contains renders from Reaper, otherwise I would probably select a different location.
So, in my music folder I just have a whole slew of .mp3's 'new song 1, new song 2, so on, so forth.' I open these with iTunes which imports it to the libary (on a separate drive) and in there I edit the tags with our artist name, an album, and I'm now starting to use comments to help keep track of them. If the version I just rendered is worse than the last, then I delete it, otherwise I just leave it in there. The 'current' version is always the highest number. When I'm done (or at least taking a long hiatus) from working on a particular song, I'll generally either delete the old version out of the libary, or at least separate them into their own album. Every once in a while I go through and clear out the Music folder as well to get rid of old renders.
I don't use a cloud service for my music (dropbox/soundcloud only) so that part doesn't really apply to me. But is there a way to tell it not to sync a particular artist or album? If you can do that, then just put your temporary versions in there and no more hassle.
Eventually I'll work out some better organization from the ground up, but for now this isn't too hard for me to keep track of.
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