I grew up as the only conservative in a family of upper middle class liberals. It always infuriated me that poor people were constantly getting free stuff, and I bought in to the whole poor people are lazy mentality.
Similar conservative here. I never really bought into the "poor people are lazy" meme. The hardest worker I've ever met was a poor Mexican who turned out to be an illegal alien. This guy was so dedicated to doing a good job I would've endorsed him for citizenship in an instant. (Likewise I haven't found the lazy, rich fat cat meme to be true either. The vast majority of rich people I know are some of the hardest working people I've met, frequently sleeping only 4-6 hours a night because they're working the other 18-20 hours. It's like they're always firing on all cylinders and don't know how to let up. Even when on vacation, they'll try to sneak off to get some work done.)
What I have noticed though is that poor people tend to make much worse financial decisions, moreso than not-poor people. e.g. A poor friend asked me for help buying a laptop. I knew he didn't have much money, he knew I knew, so I worked my butt off finding him a great deal. I eventually found him a refurb i3 laptop for $235 (when he sold it 2 years later, it was selling on eBay for $265). I felt satisfied that I'd done a good deed to help a poor person. Then the next week I learned that he'd bought a 64GB iPad for $800 (the extra $100 was to have his name engraved on it).
They don't need money. What they need is a systematic, comprehensive, plan for how to get them off the bottom. The single biggest factor keeping poor people poor, is the responsibility for children. As noted, often times, a parent finds themselves as the sole caregiver for children, and they are consequently trapped, as the responsibilities of childrearing often conflict with the responsibilities that employers would place upon employees (such as reliable attendance, and schedule flexibility). The simplest solution to the problem would be to do away with welfare and unemployment benefits entirely and replace them with guaranteed services for their dependents such as 50 hours of weekly daycare
That was exactly my conclusion too after managing a hotel with a lot of low-income employees. So many of them were single parents or were in families where both parents worked, that a good chunk of their income went to babysitting or daycare. Since the hotel usually had empty rooms that could be used for babysitting, I looked into what it would take to start up daycare services for our employees.
OMG. The legal liability and insurance requirements were crippling. Apparently parents are a sue-happy bunch when it comes to the tiniest scratch on their little darlings. Later I talked about it with a friend who ran a daycare center and he pretty much confirmed what I'd found. Liability insurance was his biggest expense, and he was always one lawsuit away from being put out of business. Eventually we just made it a policy where we would comp workers an empty room for a day for emergencies. What they did with the room was their business. If they couldn't find a babysitter and wanted to dump their kids in said room in front of a TV while they worked, and they and co-workers would check in on them every 10-15 minutes, we (management) would look the other way.