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So there are three apparent issues here.  I have 1.3.5 for windows and they are all present.  Without knowing specifically what is going on in your playthroughs, I cannot know where the discrepancy would be but I can verify these scenes are present.

1)  The sprite scenes with Raylene and Rose are present late at night but don't matter in terms of progressing the story.  You probably need to explore the basement for the special drink as part of Raylene's story (or at-least pick up the lantern) but I'm not sure.  That's when you get access to the bar's basement anyways.  It doesn't always fire (some nights they apparently aren't seeing each other, at-least not there) so you might have to make a few trips for the scenes to fire.

2)  Mary gets her adventuring costume from Rose during her story arc.  She needs it to explore the Valencia Forest.  Once you have access to her wardrobe and once you've explored the forest once the outfit should be available.  It changes he schedule so she tends the chickens in the morning and in the afternoon she's hanging out by the town fountain.

3)  You should be able to work with Raylene at both midday and at night from the beginning of the game (you need to talk to her about working for her).  Once you've progressed far enough in Raylene's story you should be able perform a "special job (???)" for her when choosing to work as opposed to lifting barrels or serving drinks.  If you don't see it yet, continue Raylene's story until it shows up.  If you're stuck at a particular point, check your journal and see what tasks you have to do.  You can always ask if you have trouble with a particular quest.

I'm sorry if this isn't much help.  Without knowing details I cannot say why the scene's aren't working for you.  If you let us know what quests you have to do, I or someone else might be able to provide more specific help.  If you're sure you're doing everything right you might want to try a re-install while getting rid of all of your saves but I think you should be able to progress without taking such a drastic step.  Let us know if you want more specific help.

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!

Mary and Rose talking with Raylene while the main character performes his special job is also something that fires at random and won't happen every time.  I don't know the frequency but it's less then half the time.  You can check to see if the scenes are unlocked by seeing if they're available in the theater in the bunny mansion (you will have to pay to open up the theater).  Unfortunately, the theater does not have dialog so you have to see the actual scene for the full experience.

I also think that who shows up is time dependent but I'm not sure.  If you perform a special job in the afternoon then Mary might show up but if you perform the special job in the evening then Rose might show up.  At-least that's what I think.  I haven't bothered to figure out what the chances one of them show up is but I would say that it is less then half so if you perform the special job a few times then one of them will eventually show up.  If someone knows the actual chance they show up then that would be great.