@1
"What is the etiquette for making draw offers when you are clearly in a losing position?"
++ If you are clearly losing, then resign, do not offer a draw. The Laws of Chess forbid unreasonable draw offers:
"11.5 It is forbidden to distract or annoy the opponent in any manner whatsoever. This includes unreasonable claims, unreasonable offers of a draw or the introduction of a source of noise into the playing area."
https://handbook.fide.com/chapter/E012018
"when people time out when they are losing"
++ They can use their time as they see fit. Maybe they are looking in vain for a way out.
What is the etiquette for making draw offers when you are clearly in a losing position? Also wondering for when people time out when they are losing. I presume the latter is so at least they make you waste minutes waiting for them to move, and they hope that you abandon the game?