1. I believe that if you develop a relationship with Kaylee, you will be able to sell the magazines to her. There is also a storyline with a photographer that (if you have the patreon version) you can use the cheat menu to access.
2. Talk to the soccer boys behind the pitch. Eventually you will get a quest to make a gloryhole in the school, which will open the option to make one in several other locations.
3. The dev has said that she is working on a walkthrough currently but has not released it. There are many questlines that I'm curious about how to trigger, I have mostly cheated my way into that content, sadly.