Night out in Manhattan will be totally ok/doable (esp 33rd or below) as you will be able to walk (or take a short uber/lyft) to the PATH. You will just need to see the schedule ahead of time because during those hours it runs much less frequently.

Brooklyn, on the other hand, can be much more difficult as you will need to rely on both the MTA and the PATH. Having to rely on one of them is risky enough lol.