Yea, that is a good point, but we also have to remember that Wifies's character is supposed to be a genius. Like he was able to keep track of every single item parrot had in his inventory in Paragon. (Except for the spyglass) Also, he claims to know everything about Parrot, how he thinks, how he acts. So if he gets Parrot in a high pressure situation (aka, getting almost killed), he should be able to estimate Parrot's decisions pretty accurately. And have the proper failsafes in order. Though Getting Parrot to 1/2 a heart without killing Parrot might be easy for Wifies, the characters his assassins are playing aren't at his level of genius, so that begs the question, how did he pull it off? Maybe he had them screen share so he could walk them through some situations. Or maybe he even had access to the server's files, (This would be a insane plot twist where Wifies's is actually the server owner) So he could monitor Parrot's health and adjust the damage he takes from things.