I think it's very reasonable to have two Diaries at once under those conditions.
Being forced to use Skills and Resources in surprising or unwanted ways is one of my secret delights in this game.
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Thanks! It never ended up being a problem I had to deal with (never lost the only diary I made) but it was niggling in the back of my mind as a what-if.
There's a lot of fine detail in this that I absolutely love (just discovered that the back cover--at least in the PDF--has been torn off revealing page 153).
My first run ended earlier today (er, yesterday, its after midnight) and my character's final regret was that he didn't have the books he owned since childhood to keep him company for the interminable eons (prompt 65 saw to that, you have no idea how painful that was). On the flip side, prompt 52 also ended up being *absolutely perfect* for him as well as he saw himself as a guardian of nature.