Thanks for this, I should have clarified more. When I had posted this, I had completed all of the story and gotten full hearts for the main six. The Raylene sprite scenes not always working clears stuff up, as I only tried it like, twice? So I guess I just need to try a few more times.
I had already had Mary wear the adventuring costume, but when I went to do the "special job" at the bar, it just played out like normal. I had gotten a scene earlier once, before getting Mary's outfit, where Rose was sitting at the bar and talking to Raylene while the scene was going on, but nothing happened with Mary at all, even after completing all hearts and doing the scene at Midday.
If that clears anything up, I hope to receive some more tips, but I'll be trying it again with the recent 1.4.4 update as well.
Thanks for the reply!