Squid plug

This is an squid shaped plug I made. I found it very hard to print because the tentacles are too organic which cause them to be fragile, or sometimes the supports would unstick from the printer heatbed.
I have printed both versions of the file but scaled the smaller one to be bigger.
On all the attempts to print them a leg or two would came of wile taking the supports apart so had to stick them again.
I found this thing to be a difficult print and a challenge for those with more experience.
I'm a printing noob so any feedback to make this print easier is welcome