Yeah, if I was in the same situation we'd divvy our stuff up between us. I wouldn't want other me to be unhappy, they'd be my closest family after all!

The characters seem to act enlightened until something personally impacts them, unless it's one that starts off with issues. Maybe they just had poor counciling sessions.

It’s bullshit that Tom didn’t immediately get promoted to lieutenant commander; Will got his rank bump for that mission; Tom deserved it just as much, if not more.

Do they explain why a hirsute adult man who’s been living alone for nearly a decade has a beard?

No.