No one is arguing for more sympathy. But 20 years of prison is not something we give those who have committed non-violent crimes, for the most part. We dont have the space or money for it, frankly. Crimes of violence are much more dangerous to society than "mere" electronic theft, and we must reserve suffiicent resources to keep all those folks locked away.
Judges have flexibility, not autonomy. Dont know the actual criteria, but likely relates to degree of mischief, previous behavior, genuine remorse expressed, and likelihood to repeat. Somewhat but not totally subjective.
US laws do not prohibit convicted felons from owning or running legitimate businesses (unless perhaps something that requires licenses, like medical or financial). We want crooks to pay for their crimes, but also have reasonable options for making a life for themselves after doing so. Having a criminal background is not easily overcome. Many businesses are reluctant to hire, banks dont extend credit, previous customers are not likely to return, etc. No need for massive govt oversight, the free markets ensure punishment is lasting and instructional
Note: I do not speak from personal experience! ^&grin