Pirated software requires rolls, so I disallow at character generation. It would also give the hacker/rigger a significant starting advantage: "Hmm, so I don't have to spend 30,000 on software..."
A pirate network contact (i.e. Seattle Cracker Underground) is a solid investment for any hacker:
Negotiate deals where you maintain updates on several programs, and trade for other updates on a rating-to-rating basis with other crackers.
or
Pay the 10% monthly/bi-monthly patch cost.
A poster on DumpShock offered the suggestion to buy two copies of each program. Crack one set and keep the other untouched. Update the cracked copies with the legal updates you download monthly. Expensive up-front but should avoid the chance of bugs.