Wild,...
With the reel in tails-out configuration, as in above photo, implied is that you'd do a full REWIND before each session, then wind the tape tails-out after the session.
In the photo above, my reel's already in tails-out configuration.
In general, the mass public thinks of putting the full reel of tape on the left side. That's normal. However you do it on the first shot is not important, as long as you wind the tape in PLAY mode all the way to the right, after the session.
Also implied, is that if you're destined to use tails-out, then you'd probably want to put the new reel on the right, so as to keep the tape on the original reel it came on, out of the box.
Beyond that, it doesn't matter that much, especially if you have a few empty reels available. Just be certain to label each tape as well as possible, plus keep a track sheet, if possible.