No, you weren't considering these possibilities in the alternative. You said he was foolish to return to Seattle, despite acknowledging that he probably had a stable situation lined up in Seattle, albeit a somewhat compromised one. You quoted Seattle's booming restaurant industry as a reason why it was stupid to leave Seattle, but then neglected to mention that booming industry when you were saying it was stupid to return to Seattle. Again, I'm not saying he made zero errors, but you're clearly contorting your reasoning to better cast this guy in a bad light.

You say he left despite "not having the means to support himself" but that only became clear to him once he got here. You're judging this with the benefit of hindsight. He thought he could find an affordable apartment in a reasonable amount of time while working full time. I doubt he expected to find an apartment right away, but he thought he could find one in a reasonable amount of time. You're imagining that he made the decision on the premise that it would be a cakewalk, but there's no evidence of that. Yet another example of you making assumptions that cast him in the worst light possible.

Contorted reasoning aside, him not deserving to be homeless is all that matters regarding feeling sympathy. I'm not saying his decision-making doesn't matter in a general sense - of course it's reasonable to inquire how he got in this situation, and of course it's good to promote thoughtful planning. But you're saying you don't feel sympathy for this guy because you think he exercised some poor judgement. The only reason you shouldn't feel sympathy is if he exercised such bad judgement to the point that he deserved to be homeless. And you already said that he doesn't deserve to be homeless. This is very, very simple.