It's really hard to see winners and losers from a fight that is participated by two famous fighters, even Jake Paul admitted that he's a fan and respects Anderson Silva ever since Jake's was still a kid. So that's already a sign that these two are only fighting for the money and the fight will result into a draw, I could be wrong, but the chances are not worth the risk.
Not sure what you mean exactly, but isn't it possible to both respect a fighter for their career or persona, and want to fight them to progress your career? Honestly, I quite like it when fighters are friendly, and have a mutual respect. Plus, we haven't really seen this side of Jake before, which is honestly quite refreshing.
It took me a while to really click onto the idea, but Jake has built his whole career, boxing, and Youtube off of a bad boy persona that basically makes everyone hate him. However, in all likelihood, he's not the same guy that he portrays.
It's an act, very much like past time greats. To some degree, Ali was an act. Jake just does it a little bit different, and no I'm not comparing Ali, and Jake just to make that clear to everyone.