Agree with the title of this thread. No idea who will come out on top after the first debate, but I will say this... Trump better be very very very prepared. Hillary is a seasoned professional with 30 + years of political experience. She can bullshit like no other and she's good at it. Trump is a street fighter and may throw her off her game with his unconventional style so that could pose a giant problem for her. He's pretty crass and loud, and she's never faced anything like that. No one has and that's why he won all the Republican debates.
I'm going to give the edge to Clinton though. Her experience and ability to bullshit MAY be too much for Trump to handle as the night wears on. It's going to be epic though. I think the entire universe will be tuned into the first debate.
A monkey wrench I could throw on your conclusions is that while Trump is getting battle hardened by extensive hostile news conferences, Hillary has been a complete chickenshit and has only been interviewed by left wing complicit bobbleheads.
If the debate team are complicit with Hillary it could get tough for Trump, if not and it's an honest debate ... Trump has far more personality and is far more change agent inspirational.