A couple of weeks ago, I had the pleasure of hearing Dr. Bruce Carlson, (of the Georgia Aquarium, and formerly of the Waikiki Aquarium), speak, and he did a video presentation which included some information on some cuttlefish that he studied - and I can't for the life of me remember what they were specifically but he stated that while they are short-lived (~2 years - longer than many keep longer-lived specimens anyway...) and he said they were ideal for the home hobbyist.
If I can remember the name or find an article I'll post it. But I was very surprised at this, because it's rare to see cuttles in the trade, but I have seen them on a stocklist.
I've seen some stores keep octopusses (the correct plural...) but IMO they are more of a "testosterone fish" for young men with something to prove. They can also ink the tank if they are annoyed or frightened, and that can wreak havoc.
I did have the good fortune to observe a femaled blue-ringed octopus brood her eggs, I watched them hatch, and of course the female was dead the next day - but what an awesome sight! The babies did not survive, but it was a really interesting thing to watch all these tiny babies emerge from their egg capsules.
The cuttles that Bruce referred to, do reproduce in captivity - he had some amazing photos of these, and he also showed some of his research on the Chambered Nautilus - my favourite Cephlopod
Jenn