Who I have the beef with, is with the writer of the solicitation. 99.9% of the time it's not the person in need. 99.9% of the time it's someone writing on behalf of that person. What's assumed is that that concerned person actually knows what's going on with the person in distress. But is it a fair assumption? How do we know if the concerned person isn't just a good-hearted person who feels that the needy person needs a fancy wedding, an expensive shaytel (wig) for the bride, new furniture, an apartment to own (Israeli thing, obviously), or a car?
The answer is - we don't. And that's sad. Because a lot of community resources can go to waste subsidizing something that the couple may not need. It's also sad because people without means will get used to getting things because someone makes an emotional appeal for them. Let me give an example:
Someone I know was engaged and about to get married. He really wanted to get a siddur for his bride - a decorated one. However, he was extremely poor. When he was at the store, he saw two siddurs: one for $30 and another for $50. He had only $30. So he started thinking about what he should do - should he borrow another $20? He meets his Rosh Yeshivah, tells him his story. The Rosh Yeshivah takes out a $20 and gives it to the bochur to buy the $50 siddur for his bride. What is the lesson learned here by the bochur? Don't do your השתדלות! Don't plan ahead! There will be someone or something to subsidize your wants!
Is this a lesson that we want to teach poor people? That they should feel entitled?!
Am I cold hearted?
The solution I see lies in organizations, not individuals. I'd rather have the poor individuals go to organizations that do chesed for people of little of no means. In the city I live, such organizations are plenty, and they're amazing in the work they do. There are all kinds of G'machs: from sheytel g'machs to wedding dress g'machs to an entire organization that will make your wedding for you - food, photography, video, and band included at cost of even below it!!! However, the needy individual has to make an effort. Maybe he needs to show his income, and yes, the questions asked and solutions offered may not be 100% what they want.
But you know what? Even people of adequate means don't get 100% of what they want!!! Not even when they buy new stuff!!! That's life.
Plus this allows people of means to give to organizations that will utilize the funds more efficiently and (hopefully) with less redundancy, and, if the organizations are non-profits, the donations can be truly tax deductible. Because donations given to a non-profit organization for a particular individual are NOT tax-deductible. EVEN if you get a receipt. This is what's written in the IRS publication 526 on this topic:
Contributions to Individuals
You cannot deduct contributions to specific individuals, including the following:
Contributions to individuals who are needy or worthy. This includes contributions to a qualified organization if you indicate that your contribution is for a specific person. But you can deduct a contribution that you give to a qualified organization that in turn helps needy or worthy individuals if you do not indicate that your contribution is for a specific person.
This goes back to my initial point: a concerned person will tell you to mail a check to "such and such" organization in order to get a donation receipt. However, as you can see it from the publication above - it's illegal.