I don't know how anyone ever didn't think Musk had Asperger's syndrome. It's almost torture listening to him speak, but I still love listening to him because the insights into how he thinks is so amazing to me.
Tiles falling off is cause for concern. What happens at the end of the much longer lever arm of the ship stacked on the booster when the booster is firing all 29 (soon 33) raptors for minutes on end?
I think an almost empty hull is vibrating at different frequencies. A fully tanked one will probably resonate completely different. And the oncoming test flights will probably reveal a completely new set of new information nobody has foreseen as of now.
He's known to be clinically optimistic. OTOH, the first orbital flight is a shot into the dark. Data collection at best, if it goes as planned, which is less than uncertain.
And I don't see much of a problem with the tiles. Reattach/replace those that rattled off and Kirk's your aunt.
I think he just doesn't care that much. His main goal for the next launch is to clear the tower before blowing up. Making it to orbit would be a mega-win. I think he's trying re-entry just because, what else are they going to do at that point?