I think (this is anecdata from some bike theft victims, including myself) that there are folks who steal bikes to ride them, potentially for transportation to work/school, and those who steal bikes to sell them elsewhere.
We should find a way to deter both groups but putting someone in jail for a $300 (let's say $600 to cover some of the unintended effects you mention) probably won't stop the commercial thieves as they'll find other lackeys to do the theft.
On a more important note, I feel uncomfortable having someone locked up, costing taxpayer money, for committing a non-violent crime whose damages are less than two weeks' pay at minimum wage.
But it's not the violence or the financial damage. It was the fact that I stopped feeling safe in my own house. That the area that I once though was friendly and safe is now filling me with dread and I was so worried about living there that year later I had to move out. That every time I heard noises in the back yard I had to get out of my bed and look out of the window. I shrugged off the financial loss of my bike very easily - but the physiological damage was much greater. Now if you asked me if I want the bike thieves to be put in prison, I would say - absolutely, positively yes. I hate and despise people who steal and I understand how deeply theft can affect a well being of a person, regardless of the value of stolen goods.
Crime occurs when penalties make it more profitable to commit the crime than not. The cost to society is paying to prosecute, reform, or lockup, people who do not adhere to the standards of the society they live in.
How about community service, at minimum wage until the work equals the value of what was stolen even if even the items were recovered? It will cost society money to manage it but it keeps the person off the street for part of the day and might teach them something useful, like being polite in a polite society
Or, it's a bicycle - keep things in proportion. Sure it sucks to have stuff stolen (I've been a victim too) but crazy disproportionate sentencing has made criminal justice in the US just insane.
Your proposal sounds great, just like all the other get tough on crime initiatives over the past 40 odd years but it has left the US with what looks like the craziest most vengeful 'justice' system outside of the Sharia introduced by ISIS.
It's all great until you happen to fall foul of these get tough initiatives - see lots of previous HN stories for examples.
I thought this would be obvious, but I am not arguing for 16 year sentences for stealing food. Food theft is one thing for which the penalty is a real conundrum (maybe the guy was really hungry).
As long as we're trading anecdotes, I live somewhere with very lenient penalties for crimes and what you describe is also true here. People typically don't even bother with a cable lock, they just use an O-lock [1] that locks the rear wheel to itself, whose main purpose is to make it inconvenient to ride off with the bike.
Also, interestingly, deterrence is not the primary reason most people push for harsher penalties. Rather it is punishment for its own sake: http://www.law.asu.edu/files/!NoTemplate/why%20do%20we%20pun...
If that was the case they would not be whipping, beheading, stoning, maiming and executing people in these countries. (spoiler:they are doing all of these things).
It's like saying because of the death penalty there are no murders in states that enforce the death penalty. When in actual fact it looks like it poses no deterrent at all.
Really? Do you have any evidence to back up that claim?
Then why don't we just give every crime the death penalty? Boom, overnight there's no more crime!
Stealing a bike is not just taking $300 or whatever from the owner. It's robbing that cyclist and would-be cyclists of the confidence to use their preferred mode of transportation, and deteriorating their health in the long term. This is a lot more damaging than non-cyclists often intuit, and insurance cannot cover it. The penalty for stealing bicycles should be closer to the penalty for stealing a car and intentionally injuring someone. Currently it's close to zero.