Thanks for your responses & tips.
VB: my missus's cousin doesn't pickle it, he cooks it on the bbq. If he had experience in pickling I probably would've asked him.
I haven't tried the blanching method yet. However, if this trick is used to break down the toughness I doubt it would fix my problem. I found the cuttly to be almost mushy.
I cooked it the same as the squid, which was:
Boil salt water in pot.
Throw squid in.
Remove after 1 min.
Place in iced water and swirl around to chill down ASAP.
Put in jars of vinegar.
Add chili, tabasco, ginger, garlic, peppercorns, etc to taste.
Put in fridge for 2 weeks before eating.
The squid turns out very nicely but the cuttlefish does not. It tastes great but it feels very mushy - almost to the point that it doesn't require chewing, you can mush it up with your tongue. Yuk.
Thanks again for the advice. I'll keep trying next time I get one. Hopefully I'll be posting results again soon.
Cheers.