I believe it is good practice to do "pro bono" work once in a while. I have been given more than one break in my career.
I make a point to donate a certain amount of prints for non profit organizations fund raisers, and give a percentage to charities from some print sales every year, even though things are tough. I see it a a defying action against bad situations and it helps people. Is it scary? Oh yes, especially lately, but it is good practice to let go of that fear.
Giving pics to a charity you support is a hell of a lot different than giving something to a business. These people asking for pics are a business. If they cannot afford to pay their bills (and yes paying writes and photographers is a normal part of doing business as a publisher), then they need to evaluate whether they have the ability to keep the business going. Businesses are, not, and I repeat, NOT charities. They need to do what all of us did when we started our businesses: Save money, get business loans, find investors to back you, etc. Asking working people to work for free so they can have a business is arrogant and repugnant. No one has a right to be in business; an undercapitalized business fails in a free market economy, as well it should.
Fine Art Photography of Indiana and other places no one else photographs.