it seems there are two different things going on here. The OP asked if he is heartless for his response to the campaign, and people are responding about whether or not we need to support someone who lost everything, or use tzedaka for valuables. And then a post about not being judgemental.
The issue of being heartless for not seeing the worthiness of the cause – I do not think you are heartless at all. I think that if the campaign was about a person who was mugged who felt bad he lost his gold watch because he knew how much it cost his in-laws, my guess is you would have cared. Your “problem” (mine as well) is that you are being asked to give money to someone who was traumatized and injured so that he could, seemingly, appease someone who cares more about his own investments than his future son in law.
There is no reason in the world that that request shouldn’t put you off. And it is not judgemental to think that such a mindset is disgusting. We are allowed to judge behaviors, and this one is wrong. Deciding the shver probably didn’t even care that he was in the hospital would be judgmental. Deciding that the guy is marrying in to a heartless family is judgemental. Deciding that there may be some serious red flags is not judgemental but a logical conclusion… if this is a true story. We don’t know who these people are, and we don’t even know if it’s true or if it was just poorly worded. Discussing feelings evoked by a narrative is not just appropriate but necessary for perspective and growth.
If this is indeed a necessity of the shver, and not just something the chosson wants to “give back” or the poor wording of the author to mean that “all is well again”, then I agree that that is tragic. But if it is not really the shver’s concern, but rather the author believed that this wording was the only way to make it matter to klal yisroel and touch them in a way that would make them give…..well that would be even worse.