IMHO the VM here isn't really the problem. Its the compiler. The way I look at it this is really a compiler bug, that only gets "activated" with this upgrade.
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bool isEntered = false;
function doSomething() { if (isEntered) { throw; } isEntered = true; ...; isEntered = false; }
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I don't really understand why they went with this gas-limit solution. I feel like there must be something I'm missing cause its too obvious.
The gas limit on send was more of a belt-and-suspenders thing, not intended as the sole protection; that may have been a bad idea in retrospect, but at the time people were pretty focused on adding every protection possible against another DAO situation.