Text Pulling apart Expression

I think I would put the text in a pre-comp that's sized to just fit the text (turning on the continuous rasterize switch in the main comp so the text stays crisp while scaling up). Then you could use a fairly simple (I think) expression to scale the precomp to fit between the tentacles. I'd be happy to help you with it if you want to try it. Do the attachment points move in the y direction (i.e. does the text need to rotate as well as scale)?

Dan