You're trying hard to be annoying, I suppose. You don't know this, but I've never worked for a startup. If you're looking for that attitude of "oh, he should have learned React and moved to SF", then you're looking in the completely wrong direction. Now, I know there are people on this board naive enough to believe things like that, but I'm definitely not one of them. And as far as "it's not my call to make", I'm not making this guy's call. The implication is that unless I have a job to provide this unfortunate fellow, in your view I shouldn't be commenting and suggesting that destroying his health by signing an employment contract that waives his right to collect damages is a bad idea.
No, I'm not. That's called 'disagreement' and it can happen.
The only thing I note is that you don't know what options this man has available to him since you are not in his shoes and you can simply assume that he's trying his level best to do the best he can - just like everybody else. So unless you wish to increase the number of options available to him I don't think you should be telling him what to do, just as he wouldn't have any standing to tell you what to do.
None of your other assumptions are relevant to this and besides I wasn't making them.
Filipino employees are exploited because they have very little in terms options to resist signing such contracts. It's akin to victim blaming.