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You're welcome. The game is still 100%able even without this specific combination working. But I figured others are also bound to run into it on their playthroughs.

I just grabbed the most recent download, 1.14(2)

I was able to confirm that other medium endings work just fine still. I was even able to finally see the tentacle potion in action. 

So I decided to start again and go for the specific ending combination that was causing the looping and I can confirm that even on 1.14(2) the looping still occurs. 
By beating Gummy, Crusher, and winning Jester's Game day one
Night 1 I just make a potion. 
Day 2 I beat Gummy again, make the feeding potion so the Leezard stays and I don't get Poko. 
Night 2 I beat Crusher a second time. 

This results in the three being wimps to me in the Grove, as expected. But they still have the Lizard on their side. When I speak to Jester to initiate the Medium Ending sequence it will begin to fade to white before stopping, and leaving me able to speak to him again to initiate the ending. On loop. 

This is the only ending sequence I've had this occur on. Specifically where I've bested the Jerks, but did not rid the Beeg Lizard. 

I ran through on a new game from tutorial to the grove (Dialogue skip made that easy, tysm) and when I talk to Jester to confirm that I'm done messing around it starts to fade to white before resetting back to before that conversation. This time I even forgot to swap out the potion (I'm realizing now).

The issue seems to persist.
I can try going back through the entire game making the same choices, but that'll taking longer than loading the save already at the grove. 

I feel like it might be because we defeated all three jerks but didn't scare off the Beeg Lizard. At least that's what it sounds like since the potions are different and therefore unlikely the source. And I've also gotten a ton of different medium endings, just not one where I defeated them and kept the lizard around

I've 100% the game but noticed there was a tentacle potion thanks to the comment. I started up a new save, ran through real quick going while defeating the jerks. I beat Jester's game. Made the dark potion at night. Forgot to check their pc.

Fed the Beeg Lizard just the feeding potion, didn't recruit Poko. But I did swap the potions out.
Crusher is tiny and no one attempts to bully me in the Grove. I paint the flags. Can't do the password of course. 

After that I talk to Jester and like above it loops me back to before I started the conversation with him to initiate the ending. 

This would also be a medium ending. 

I have updated. 
Sorry for the long post, I just wanted to provide the specific triggers my ending is on incase that matters at all. 

The game is lovely. I've had a blast seeing all the different endings and variations in the medium endings. 

I actually have zero memory of what you're referring to. 
I own MV rpg maker and enjoy snooping around the maps a little too much. 

Are we ever gonna get the jackoff spot moved somewhere we can access it. >.> Yknow. the one in the middle of the water on the docks map. >.>

Sweet. Glad I could help. Can't wait to see more of this. I may have gone through a ton of the current gameplay currently. (and slowly need to scour to see if I've missed anything)

Minor Bug.  On the Normal Fighting Route near the end you encounter a large group of enemies. 3 regular Hyenas and 2 of the Yellow Jacket guys that wind up their attacks. It's clear they're meant to alternate their wind up to give this fight some challenge. I even lost the first time. I came in the second time and used two of the Hard Times attack. This managed to knocked out the first guy before he finished his attack. Afterward the second Yellow Jacket Hyena simply stood still. I left him for last and was free to focus up back to full and then attack him without him ever winding up for an attack.

My guess is because I never let the first guy finish a trigger on the second guy didn't occur.