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https://steamcommunity.com/sharedfiles/filedetails/?id=1283977160
If you ♥♥♥♥ Madison, Derek will no longer give correct advice for other quests. This makes it difficult (if not impossible) to advance quests like Frank's humiliation. It will also be much more difficult to get anywhere with Amy, because Derek is needed twice for the scavenger hunt and he also makes Amy think you're a racist. This will hurt your relationship with her - if you aren't friendly with her at this point, she will outright refuse to talk to you ever again. And if Amy doesn't trust you, then you'll get stuck in the middle of Leah's quest line. Some of these things can be fixed, but this requires decisions and resources that will close other opportunities.
If you don't ♥♥♥♥ Madison and keep Derek friendly, then all these opportunities remain open.