Unfortunately, breeding cuttles is still a one-off occurance and you will only find captive bred on rare occasions (subscribe to the cuttlefish availability thread for email notifications of both captive bred and wild collected egg postings). The most typical keeper will start with wild caught eggs and may be successful with eggs from their tank raised hatchlings but we don't see continued generations ... yet.
Tank bred octopuses are just not going to be available, now or anytime in the near future. The most common, easiest to raise are the large egg Gulf dwarfs (O. mercatoris). We have had two generations (WC female -> tank born hatchlings -> tank bred hatchlings) raised by several members but the survival rate has been only 4 or 5 for each brood and keepers opt to raise the surviving animals. Tank mating anything other than the mercs is problematic in both tank capacities and finding suitable mates. Additionally, only the large egg species have been successful (minimally) even from WC females. The most successfully raised hatchlings (again WC female, I don't know of a successful breeding attempt on TONMO) have been bimaculoides, however, these are very hard to acquire as they are primarily from California and may not be captured there and sold (they can be legally captured with a fishing license then used as bait, eaten or kept as a pet by an individual but not sold alive). Additionally, they require cold water (below 69 is best but viable at 72 for a shorter life span). We occasionally see hatchlings available once every couple of years. Most of our octos come either from south Florida or from Indonesia. The Indonesian animals are typically A. aculeatus or an undertermined nocturnal in the Macropus complex. From Florida, O. briareus with a sprinkling of O. mercatoris, O. hummelincki and O. vulgaris are most common (prior to the earthquake, O. hummelincki was also imported from Haiti). Subscribe to the octopus availability thread for octos for sale spottings.