There is a certain gheyness attached to some of the content you listed, I think there should be a balance between to keep the place fun and not turn into a full-blown "discord imageboard" as you call

I have to agree some of those backpack pins are stuff that'd be deleted out of tumblresque lame-ness, but they're also in the context of a crazy girl posting about the anime she likes. I'm happy Heyuri users do a good job not talking about those parts of otherwise acceptable occurrences

I didn't particularly check their background but the crossdresser who posts his nudes is seemingly a Heyuri regular, it can't be all his identity. If it's his fetish to post n00dz while shoving a dildo up his ass, we'll let him! Everything aside, such sexual content is always welcomed (to the extend of not having the board domination, or doing it in a certain way u see on 4/soc/) on Heyuri, whether the subject is hawt girls or bara yaoi is up to our luck

some other points
>a bunch of namefags with mod-given capcodes
lurk moar - "namefags" are always welcomed, and capcodes are to encourage it (and a special feature of our board software, though 4chan used to do the same in teh past)
>There is one thread about people meeting up, where they talk about doing so wearing cosplays
As with all real-life events including Heyuri, it would be a hueg win! You're just partyp00ping.
>I am half expecting a mod to delete this since I think at least one of them is a crossdresser himself
Not to my knowledge
I understand you're genuinely worried and have a good will, but if you're worried about your posts getting deleted, consider trying to follow the rules instead of (falsely even) calling any people in a rule 7 way.