I understand the resentment, but there's just a couple little problems
In response to your "First". Have those in this scenario sold ALL of their "toys". Computers, iPods, motorcycles, boats, second car, etc., etc., etc.?
'Toys' is a [negative] value judgement that I wouldn't feel comfortable making - who should do that? One person's toy is another's need: for instance, a computer and cellphone are invaluable for finding and obtaining employment. An iPod may have been a gift, or prize - should that be taken from them? All kinds of thorny knots in that subject.....
Or, as in most cases, have they decided they "need" these things AND money out of my pocket? If they are unemployed- almost EVERY area of the country we travel has plenty of "Now Hiring", "Help Wanted"......... signs.
It's rather a stretch to assume that 'help wanted' signs equal a job that would lift a person out of dependency. I just read of one man who has worked at the same McDonald's for over 20 years [!] and is still filling in his dietary needs at the local food pantry almost every week. Why? Because first: the job requires 'flexible' scheduling, meaning the hours & days change every week. That keeps labor cost to a minimum, but prohibits workers from getting a second job, too. Second: the McD's is a franchise that has been bought & sold many times in those 20 years, and the first thing every new owner does is cut wages back to minimum, no matter how long the worker has been there. So this guy has over 20 years seniority and is still making minimum wage. What would you suggest he [and many thousands just like him] do to get himself off the merry go round of poverty?
If they are on anything short of unemployment (had been working and lost their job- NOT quit!), anybody on government assistance should be FORCED to take an available job, or OFF the assistance they go.
Underemployed- get a part time job or two. I have been through some very tough times myself. For years and years, I held a full time job and THREE part time jobs at the same time. I have lived with a friend for a few months, to get on my feet. I have lived with family for a few months, to get on my feet. I DID NOT go into your pocket!
I've been there, done that too: worked several jobs and lived with family or friends - I know how it works. But I also know that every situation is individual, and there are some who cannot do it. The flexible scheduling is becoming very popular among the fast food, retail, and other industries [like the guys at Blue Beacon, the aides at nursing homes, etc] that primarily hire low wage workers. And many have no family or friends who can accommodate their families [spouse & kids] because every one they know is in pretty much the same boat. It's easy to say they 'should' do this or that, but it assumes a LOT of facts that you don't have, and is therefore probably wildly inaccurate.
Did the 2 owners you once drove for have medical insurance? Too many opt for the fun things in life as opposed to the responsible purchases. I know a whole lot of "I can't afford health insurance" people who have a cell phone, computer, Play Station, motorcycle, boat, guns, vacation time-share condo, etc., etc., etc.. And no insurance- then we are to feel sorry for them when they have serious medical issues and can't carry on without our help. (And they usually keep all of the above mentioned items too!)
Both had insurance. One was diagnosed with cancer that spread, and has passed away, leaving his spouse with some major financial liabilities. The other lost her spouse to the same cause, struggled to keep the business going, then was seriously injured in an accident and lost what little she had left. Both were hard working people who suffered a lot, in spite of trying their best to do it the right way. And there are a whole lot more just like them - waaaay too many, in fact.
Churches, FAMILY, friends and those whom CHOSE to donate, use to be the pockets for the "assistance" people received. Now it is ROB from the responsible workers to give to the irresponsibles.
Again, that assumes everyone HAS family and/or friends who are able & willing to 'help' - [like Romney suggesting the solution to high college tuition is to 'borrow from your parents' 
], and that they're just not smart enough to have thought of it. Fact is, most people associate with 'birds of a feather', so their families & friends aren't much better off either.
When charity was exclusively the church's domain, people who applied were required to accept the religion along with the food & shelter. For that reason, but even more because so many elderly had zero savings or family to rely on in their retirement, the government took over the majority of the financial assistance. It is society's problem to solve, and I agree that employment is a major part of the solution. So does every state that provides benefits, BTW - there is NO free lunch.
Having said this, I have donated on MANY occasions. To charity organizations, and to individuals on the street. But, these are donations I choose to make- not that I have been forced to make
The reality of taxes is that everyone is required to help pay for things they would rather not - we don't have much choice in how the money is spent. [I'd like to stop contributing to foreign aid for quite a few countries, myself!].
Those whom see nothing wrong with helping EVERYBODY should be allowed to. Those who DON'T want to help EVERYBODY should NOT be FORCED to!
Now, don't get me wrong, those who REALLY need help and CAN'T do for themselves do need help. NOT THOSE WHO DON'T WANT TO WORK!
