Dave's lying when he says, "Listen to people and believe them, it's not complicated." Dave, as a frequently exposed liar above and beyond his whole True and Honest Woman posturing, wants people to listen and believe and then give him gifts of cash because he claims he needs it. Funnily enough with so many e-beggars, troons or otherwise, that "practical gift" of a gas station gift card wouldn't be well-received, because they're lying about what they want the money for. By giving them "something they'd actually appreciate", you're not buying them something for you or for them, because they want to spend that money on something else that sounds less of a noble cause than their bills or car for work.
I'd never buy Dave a gift. I don't want to help him reach his "goals", and even if I knew nothing else about him, his added comment about privileged people would mean it's clear he doesn't actually believe the thought counts, he just wants other people to make his life easier because he's thinks he's entitled to free stuff. But I'd guarantee that if someone gave him a gift card for gas when he complained about not being able to fill his car up, he'd be angry - because that's helping the stated problem, rather than the real problem, which is he just wants money and he expects you to give it to him when asked.
So, if forced to buy a gift for Dave or any other frequent e-beggar, always give them what they say they want rather than the cash to buy it, which is what they asked for. Because it's always fun when they actually wanted a $50 shirt but you've 'listen and believed' their sob story and they've gotten a practical gift instead that can't go on anything other than the lie they were using to grift. They get so mad...