It’s both difficult and easy to be a libertarian.
It’s difficult because the corrupt Washington establishment of politicians, lobbyists, bureaucrats, and interest groups almost always is allied against us.
But it’s easy since you have strong moral principles that put liberty over statism, so at least you don’t need a lot of time to figure out whether class-warfare tax policy is desirable, whether the federal government is too big, or whether government should be throwing people in jail for victimless crimes.
But not every issue is black and white.
About two years ago, I made fun of the bureaucrats in Montgomery County, MD, for proposing a plan to require that bums and panhandlers get government permits.
Afterwards, someone from that community told me that the goal wasn’t more bureaucracy, but rather to give local authorities a legal excuse to take action against vagrants who supposedly harass other people.
I don’t know if that was an accurate assessment, but it does raise an interesting question of whether the government should have any laws to limit panhandling and discourage people from becoming bums.
The local government in Houston seems to use this approach. As reported by the Daily Mail, you’re not supposed to feed vagrants, and it’s also against the law for bums to rummage through garbage.
A homeless man has been given a ticket for rummaging through a trash can in the downtown area of one of America’s biggest cities. …The summons he was issued cites his violation as: ‘disturbing the contents of a garbage can in downtown central business district.’ …the city’s laws which ban the feeding of homeless people… In most other cities homeless people are able to rely on the kindness of strangers for food and those who have fallen on hard times are free to dive through the garbage at will, but in Houston even that source of food is banned.
By the way, this issue isn’t limited to government actions. Some business owners in normally liberal California have become so irritated by aggressive mooching that they have distributed stickers saying “Please don’t feed our bums.” 
So what’s the right policy? Is there an unlimited right for people to be bums and aggressively pester others for money? Does that include a right to sleep on the sidewalk, even if that undermines local businesses?
I confess that my gut instinct is to oppose such laws. On the other hand, I don’t like being harassed by able-bodied men who don’t want to get jobs. And I would be very irritated if I owned a small business and was losing money because bums were driving away customers and causing property values to decline.
If you like these “you be the judge” quandaries, here are other examples of difficult-to-decide issues.
- Is it appropriate to put politicians on trial for economic malfeasance?
- Is it excessive vigilante justice to set your daughter’s rapist on fire?
- Should prisoners with AIDS be segregated from other convicts?
- Which tax collection tactic is more brutal and unjust?
- When a wheelchair-bound guy uses a baseball bat to punish his granddaughter’s molester, what’s the right response?
- Should politicians set pay levels at government-owned firms?
- Is sharia law sometimes appropriate?
- Is the Netherlands right to segregate troublemakers from the general population?
- What do you do about self-destructive behavior in a government-run healthcare system?
- Should there be laws against incest among consenting adults?
- Should motorists be allowed to warn other drivers about speed traps?
- Is jury nullification the right approach for victimless crimes?
- Was this angry father wrong to take matters into his own hands?
- Should drunk-rafting be a crime?
- Should rich people pay higher speeding fines?
I tend to be guided by the sentiments in this amusing poster, but many of these questions defy easy answers.
P.S. If you want a good chuckle, check out this entrepreneurial bum.