I ran a small consultancy for about 15 years and came away convinced that is the way to go for folks that can't get work because of a criminal record. Even though we were entrusted with some pretty serious information (we were in infosec), none of our customers except for one large bank and the federal government did any kind of independent background checks or insisted on any specific hiring practices. I think you probably need the facade of a brand instead of just Joe Blow, independent contractor, but most people just trusted it. We did have a few customers insist on E&O insurance, which may present some challenges, but most didn't care about any of that.

This might seem like a million miles away from where you are now, but if the skills you have or can develop are marketable it might be something to look into...if for no other reason than to give you some hope.