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The biggest problem I need to be careful of is the Twitch ToS.  I need to make sure that all games I play on stream follow it carefully, or I can potentially lose my channel.  Twitch is weird when it comes to nudity, wherein games like Witcher 3 is allowed, even with the sex scenes, but say a Hentai game is not so much allowed.  To reference the exact rule they have:

Sexually Explicit, Adults-Only, and Other Prohibited Games
Nudity, pornography, sex, or sexual violence can not be a core focus or feature of the game in question, and gameplay with modded nudity is entirely prohibited. Occurrences of in-game nudity are permitted, so long as you do not make them a primary focus of your content and only spend as much time as needed in the area to progress the game’s story. Games rated Adults Only (AO) by the ESRB are not permitted in content on Twitch.

A remake of Custer's Revenge is going to fall strictly into the "Sexually Explicit" category, as it's literally a game about raping women.  I am not going to have to say that no, a remake of Custer's Revenge is not allowed, as I plan on showing the game each game is based on on-stream before playing the game itself, and I cannot possibly play Custer's Revenge on stream due to the Sexually Explicit nature of it.  For the record, I am not one for censorship in video games, and I personally have no problem with offensive content in nearly regard, however, I've got to play by Twitch's rules.

I'm going to expand my Game Jam rules to include "No Sexually Explicit content" thank you for asking first!