When Sasuke is assembling on the rooftop, why does Hinata not have a single concern letting Boruto go into the portal? I'm not saying she failed him by not worrying but it
is odd.
You must be registered for see images
Sasuke, the outlaw nomad who changes sides often and is hardly the most trustworthy person in the Leaf....claiming that this academy kid is ready to fight a 2 gods who hospitalised her, the Jonin. That's a LOT of trust to place in Sasuke, this dude who just shows tf up to look after your kid in a battle they dont know whether they're going to win or not
You got some things wrong:
1. Hinata did worry. In fact, she wasn't even going to allow Boruto to go. Then she saw Boruto in Naruto's part 1 jacket, and after seeing his resolve and getting some slight assurance from Sasuke, she let Boruto go.
2. Sasuke is no longer an outlaw, and he doesn't change sides often. It may have been a 15 year series to us (the readers) in real time, but in universe (from the perspective of the characters themselves), Sasuke's rouge ninja phase was just a brief period that only lasted for 3 - 4 years when Sasuke was a kid/teenager. That point in time was over 14 years ago relative to the point in time of the Momoshiki arc. Even during that time period, Sasuke mostly did good for the shinobi world. He defeated multiple akautski members and even briefly "killed" Orochimaru. His only dark phases were his crush Konoha phase and to some extent his "revolution" phase, and those phases lasted only a couple of weeks at best (actually the latter phase was only a little over a day).
Don't be fooled by our real life time. Remember, in - universe the war only lasted for 2 days and ended on Naruto's birthday.
I'd hardly refer to a teenager that alters his goals over the course of a few weeks (after hearing some traumatic revelations) as "switching sides often".
3. Boruto was not an academy student. Remember, this was the chunin exams that Boruto had just taken, meaning that he was a genin (before Naruto took his head band).