I have no experience with cuttlefish either, but I do have experience with squid. What I've learned is that size makes a difference, smaller is more tender, and cooking for a very short period of time keeps it from turning to rubber. I cook the breaded rings for 2 1/2-3 minutes... about the same time as clam strips.
With a cuttlefish being a cousin to the squid, my guess would be that they could be cooked in similar ways, so you might investigate some squid recipes and read about what they say.
It's just a suggestion.