That would be helpful. It is of course entirely your prerogative as host as to how you put your playlist together; but as you've asked "does it matter?", this is why I prefer a playlist to be presented in oldest-newest date order - I can of course only speak for myself:
I use a playlist to save me having to click on individual entries separately. I use it after I've caught up with on the posts on the forum; or to play a Season's entries on loudspeaker while I'm doing things around the house. I might visit a Season's playlist 2 or 3 times in a week. When I visit a Season's playlist, therefore, I want to use it to pick up from where I left off, to listen to the entries I haven't yet heard. If the list is in reverse date order, I can't do that. Youtube doesn't give me the option to reverse the order in which I listen to the playlist; so I can't use a playlist arranged newest-oldest to catch up on what I've missed. It's like trying to walk up the down escalator.
Like I say, it's entirely up to - but you did ask!
