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I'm a bit stuck on Rinny's quest, it seems obvious the loosened gravestone is the key but I can't get past her objections. Do I need to find a way into the graveyard without Rinny? Become better friends with her?

You will find a mirror at one point and if you interact with it you'll get an option for it to take you or Rinny.

I think I remember something like that happening on my first playthrough but it took me. Did I fuck myself over raising my mys level too high before trying it this time?

No I have a high mys level too. I just kept wandering around till I found the mirror.

Getting Caught is a Bad End. 

Get Rinny, caught to continue the Storyline.

Ah yes, The Pink are indicators for the Right Path, however one Pink Path will try to Bait you.

So Look out.