There in lies part of the problem. It is not as simple as you make it sound. While I 100% agree with you that honesty upfront is the absolute best approach, the problem is that 9 out of 10 times employers simply scan applications, see a check for conviction/arrest history, with or without notes explaining the circumstances, and discard the application. So while the applicant may have taken the best approach, it often doesn't work out for them.

The real problem with background checks is that there is loose regulation around them. Often times these companies return inaccurate or incomplete results. Often times they provide reports that are not in compliance with FCRA. An even bigger problem is that a background report provides absolutely no context to a crime. They also make it difficult at best to dispute any mistakes. This is a huge problem.

GoodHire (a Checkr competitor) are working to change this somewhat. They allow individuals to add notes and context to their own background reports. This can be done individually (the person pays for their own report and adds the notes) or after a background check is provided by a company.

Disclaimer: My company is a GoodHire partner.