Hello! This month has been a whirlwind of unexpected bugs and technical limitations, but some solid progress is finally emerging! After lots of trial and error, I figured out a method to proceed with larger sizes. 
At a certain size, I replace part of the body with a new mesh that uses the same softbody simulator as the blob sizes. This new mesh rides along with the character rig and has some hook points that follow the movement of the arms and legs. Once in this mode, the character can continue growing much larger and has the benefit of higher jiggle fidelity like the blob sizes.
Unfortunately this broke a ton of stuff so I had to rewrite a bunch of code to accommodate. Here's a few of the more hilarious problems I ran into.

Most of these issues are solved now so the hardest part is over! There's a couple minor things that still need to be hooked up and I want to go back and refine the new body mesh around the arms and legs and include the thighs in the simulation as well.
While closing the gap between skinny and blob, I'm considering ways to facilitate the growth from one phase to the next. There are some points in the growth where the entire character needs to be replaced with another version that's capable of growing bigger. This causes a harsh transition. (kinda like when you switch from skinny to blob) I've tried lots of things to avoid this and make the entire process smooth, but I've discovered that's simply impossible.
To work around this limitation, I'm planning to add a sort of level up system. Each phase would have a weight bar that you fill as the character gains weight. Once it's full you will get a point to spend on "evolving" your character to the next weight level. The character will not gain additional weight until you spend this point to level up. Spending the point would trigger a flashy level up effect that would hide the harsh transition to the next phase.
I want to include a basic version of this in the next build, but long term I imagine a system that offers several choices you can make when leveling up to the next size. Think something like a skill tree with branches. Early on you would choose a general body type to "evolve" into. As you level up, options branch off to a few variants of each body type. (e.g. a big boobs version of the wide body) This is still a long way off of course, but in the end it would allow for a lot more variation in body type while navigating around the limitations of transitioning to them smoothly.
Anyway, I should have a new build with a basic version of this in the next week or two. In the meantime I'm interested to hear your thoughts on this direction and I appreciate your patience while I figure these things out.
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