It's the last one that makes me wonder. Because of course, how did R. Eleazar b. Harsom manage his great wealth? Why, of course, he hired other people to look after it for him (my Rabbi even said that in his sermon.) To which I might ask, what if the Heavenly Court tries this on someone and he says, "I know, I was one of the people he hired!" R. Eleazar is to be praised for hiring people to look after his possessions... but the people he hired are to be reprimanded for being hired by him‽ It is praiseworthy to cause someone else to "sin," so long as you don't yourself‽ I'm not really happy with answers I hear. In a sense, R. Eleazar is essentially selling his "wasted time" to me, so he won't have to deal with it, or even more accurately, he's buying my Torah-learning time to fill his own needs. I'm guilty because I'm selling? Or am I therefore claiming poverty, like Hillel? No, because then I should be listening at skylights of houses of study, and then where would poor R. Eleazar be?
Should we say, then, "well, that just means that all real work is supposed to be done by gentiles, and we Jews are meant to sit and study all day"? Against that, in addition to the general moral repugnance I feel at racism implied in that viewpoint, there are also Biblical verses, "Six days you shall labor" (Ex. 34:21), "For six years sow your fields" (Lev. 25:3), and the same sentiment repeated all over the place. It would seem that doing work is actually a commandment, so what's the problem? (Apparently there really is an opinion that Jews are only supposed to be studying, and actually doing things is to be left for the hoi polloi/gentiles, but that isn't the way the law goes, and there are lots of rabbinic statements against such an attitude).
OK, OK, I know, I guess the real answer is that I'm over-analyzing. The point of the gemara is "don't make excuses for why you didn't do better, there's always someone else who has it worse than you (and maybe is managing anyway)." I guess it just strikes one wrong hearing it put this way.
I think in a broader sense this reflects an attitude that one sees a lot not only in religious outlook but basically in anything reasonably old. It is a comparatively new concept that all people are even approximately on equal footing (or at least that such an idea can be taken seriously). An old cookbook remarks that beating eggs or something is a strenuous task, and should therefore be delegated to a manservant (what if I am the manservant? No advice for me then?) The Code of Hammurabi says that if a craftsman kills someone's son, then the craftsman's son is to be killed. But isn't everyone someone's son? I guess here the implication is not a class one so much as an age one: when they're underage, children aren't full people yet, and we don't punish according to the hurt you do to them, but to the hurt that hurting them causes to more important people (their parents).