Jumpin' JellyFish! That was tentacular!
The use of shape keys and vertex groups was an awesome bunch of training nuggets I think I am finally ready for. Super cool Kent. Still works great in 2.8
Side note: I felt like the fewer verts I had for the cloth base mesh plane improved the tentacle base during the first part where you deform via cloth physics and shape keys. I actually left one of the sub-div mods off and kept the other at 1 subdiv and placed at the end of the stack after the cloth modifier because it was making the ruffles bunch together way too much.
I also found that the loop tools add-on bridge function helped the mirror for the top to bottom for the array modifier better because it would try and extrapolate the curviness to the bottom verts with one of the options enabled.