I agree with what the other guys said so I’ll just add a little of my own personal experience to balance the pros with the cons of being too generous, which it sounds like you’re already somewhat aware of.
A few years back we hired a PA and I later found he had lied about everything to get the job (work he presented as his own wasn’t, didn’t know any of the software or gear, etc.). I could’ve easily gone to our boss and told him this kid can’t even white balance a camera or make a new layer in Photoshop so we really should cut him loose. Instead, I held the kid’s hand for the next 2 years teaching him literally everything he needed to know to do his job (which he apparently confused with me teaching him everything I know). I introduced him to all the right people and resources he’d need to learn more and even spent nearly half of my budgets to get him set up with the right tools (i.e., buying two relatively cheap computers instead of one better one for myself, two Adobe suites instead of one and the new monitor I needed, etc.). Since it was the way all the PAs I had worked with reacted, I figured he’d be glad someone gave him a shot even though he hadn’t earned it, build on what I’d taught him and do a bang up job for us for at least a few years to come. But, of course not … he chose to sit and do nothing … as I had to do the double workload that was expected since we had more people. What’s worse is he had learned just enough to be dangerous … enough lingo to make it sound like he knew what he was talking about (at least to those who can’t tell the difference). So, he tried to convince everyone that, after only 2 years in the biz, he was somehow magically qualified to replace someone 20 years his senior … me! When he realized that there was a significant portion of both our jobs that he knew nothing about and couldn’t even fake without me around, he ended up quitting for fear he’d be found out once I stopped letting him use me.
My point is giving back is definitely worthwhile since we all had to start somewhere, but be selective and careful. As you suggested yourself, you had to earn your way so there’s no reason others shouldn’t have to. I finally had to ask myself, is it really wise to help someone take food off my family’s table? I consider the COW a little different since so few of the people are in my same market.