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DaasYochid:
First of all, I did not express a position. I merely asked a question on the existing position(s). Second of all, the fact that it is a test doesn’t make it devoid of meaning – the test is whether you will obey the Divine will and the meaning is in obeying the Divine will. Or the test is a means of earning reward and the reward is the meaning. Third of all, why do you assume that something has to have meaning? There is no intrinsic Godly quality that demands omnibenevolence. Theoretically, an all-powerful God could just torture you all day and your life would have no meaning. Luckily for us, Hashem is nice and allows us to benefit. Fourth of all, you are equating “meaning in fulfilling a commandment” with “reason for the commandment”. If you want to give an example of a particular mitzvah which Chazal or the Sefer Hachinuch explain how it has meaning, we can discuss it.
I think I did address the chiluk between WOULD and SHOULD by expressing the lack of hechrech for there to be a chiluk.
As for your last paragraph, of course there has to be a point where you can no longer ask why. That point can be “pleasure”, “benefit”, “happiness”, or something of that sort. Any decision can come down to a cost-benefit analysis. You decide based on what is the most beneficial to you. I’m not saying that you have to pursue benefit, but you don’t need a separate reason to explain the pursuit of benefit.