I do believe he enjoys the situation to an extent.
I remember him saying as much during the end of the Annafrills saga. I believe it was when he was having a struggle session with Brittany/Aba/Melina about why he gets into these situations. It may have also been after Melina dipped.
To paraphrase
[I am at my best when I'm going through drama, it's when I feel like I'm firing on all cylinders]
I believe he walked back those statements since the Vyvanse RX and blamed those self destructive tendencies on undiagnosed ADHD. Shockingly it seems that covertly recording and leaking sexual exploits is not in fact a symptom of undiagnosed ADHD.
I don't think he consciously tries to fuck over his future self, I think he is just a full on retard struggling with his insecurities who has constantly been buoyed by his ability to get away with it.
He's self aware that he is a manlet with an Earthworm Jim dick and if he was cleaning carpets he would be begging for sex on tinder and posting on incel forums in his spare time. He is aware that he fell backwards into fame and money and that's his only avenue to BPD pussy. His need to show everyone his sexual exploits is his way of covering up his insecurities over being an earthworm Jim dicked manlet.
It should have been over with annafrills as he was sexting a girl he was calling a stalker in livestreams. But it didn't end for him there so he continued to leak and exploit because he never had a consequence. He needs the audience and importantly his orbiters to think that he is a mega chad, blowing who he wants, sexing bpd whores and onlythots, and that these things are desirable for the average person. Think about his diatribes about how herpes and STDs aren't a big deal and are way overblown.
Now a married adult like I may be looks at that lifestyle and say "actually giving my wife herpes is a nightmare I couldn't live through and having to handle more than one person intimately seems completely insane especially when you are a parent."
Destiny would probably call me an incel for that statement because inceldom is his biggest fear as obviously a lot of people he fucks that aren't on the grindr set have to be compelled. His personality is grating and dull, he has a 15 year olds view of sex and drugs, he's short, his dick is weird.
My biggest proof is anecdotal, but for the married adult men in this forum, when was the last time you had even an explicit conversation with your peers about your sex life? I don't think I've had one since high school, it's not a very interesting topic. It takes a high schoolers mindset or deeply insecure mindset to not only share the details, but photographic or video evidence is just another level of tryhard IMO. The only reason I can think of to share that is because you don't think anyone believes you, and honestly someone who was unaware of Destiny's e-fame listening to his bed notch list would never believe him.
Tldr
I think destiny wants people to think he's a lothario because outside of his money he's very undesirable. He's addicted to people thinking he has game when in reality he knows he just has money.