As far as I recall, getting legitimate licenses is just a matter of time and paperwork. A sane DM would probably just include legal fees in your extra lifestyle costs.
Besides, getting things licensed on your real SIN means it's traceable to you. So be careful which items you register to each SIN. The game suggests having one SIN you use for innocuous/legal activity like eating and going to movies, so your real SIN should work perfectly for that.