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    \$\begingroup\$ Your question is quite long and chock full of details that, while colorful, risk distracting from the heart of your question. Would it be fair to distill this question down to "How do I simulate the effect of intense and ongoing nightmares on a character without over penalizing the player?" \$\endgroup\$ Commented Apr 29, 2020 at 21:49
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    \$\begingroup\$ @Rykara I think the source and nature of the nightmares are helpful context, in which case the question becomes "this is the narrative I want to make - are there rules/mechanics which support it?" \$\endgroup\$ Commented Apr 29, 2020 at 21:56
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    \$\begingroup\$ (1) Have you ever DM'd before? (2) I have edited your question since the prose is awkward and hard to follow. Please review the edit to make sure I have correctly perceived your intended meaning. Did this player do something that has evoked a desire in you to punish them? After reading your idea of "fun" I am lost as to your purpose. \$\endgroup\$ Commented Apr 29, 2020 at 22:51
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    \$\begingroup\$ Is it safe to assume every instance of "player" in the question should read "player character" (or just "character")? Mainly I want to confirm that these negative effects are meant to impact the character, not discourage/punish the player. \$\endgroup\$ Commented Apr 30, 2020 at 3:25
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    \$\begingroup\$ If the player is at all experienced, they will recognize that this is a dream shortly. Unless you're a very good gm, the player may not like it. This sort of thing works very well in a book or movie, but this is none of those. It is a game. \$\endgroup\$ Commented May 1, 2020 at 0:23