Though Gibson's record going all the way back to Opcode is not too good, I suspect they may have tried to sell Cakewalk before closing it. Anyone know what was done? Would Craig Anderton be privy to that kind of information?

All of your questions have been answered over and over again.  Search the forums here for the Reddit thread from an ex-employee for the full story.
 
Answers:
 
1)  No Gibson did not try to find a buyer for software that was losing money.
 
2)  That other Craig was not privy to any "private" information and has expressed his opinion plenty of times here and other places.