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(+1)

You can find your saves in  /(WhateverIsYouHeadmasterFolder)/game/saves. First number in the name of the file is page, second is slot of the save. That being said, you don't need to do anything specific – update doesn't delete your saves.

As for the second part... Idunno. Don't remember, rather. Rule of thumb is to try and clear other quests in hope it'll unlock the path or something, but other than that I can't help.

I'm new to using Itch.  So do i just extract over top of the existing version replacing the files

That should work, just transfer the save files to the new folder.

tysm

(+1)

Not sure either, but on the second question, passing that rule triggers Mycock showing up and the transition to chapter two, so you need to have Debbie finished, and several other girls advanced to a certain point (all the girls that you can ask Trixie about, I think) first.