Thanks @meta87!
So I know you are all on the edge of your seat for this, so here it goes.
It turns out, Delaunay Triangulation by itself is a good start, but the link to the research paper I posted before is for Delaunay REFINEMENT algorithms, which take place after the original Delaunay triangulation and are very iterative, going through and cleaning up non ideal triangles and so forth.
They are kinda fascinating, if you wanna read more.
Ruppert’s Algorithm Delaunay refinement - Wikipedia
Chews 2nd Algorithm Delaunay refinement - Wikipedia
These are awesome algorithms, but are not included in any of the c# poly2tri implementations out there, and I am also not sure if mobile can hang with them. They were however, added in the C version of poly2tri within the past year, dubbed the Delaunay Terminator Google Code Archive - Long-term storage for Google Code Project Hosting.
Another side note, Adobe After Effects puppet tool has a really boss triangulation algorithm.I have no idea but would guess it uses one of these algorithms or something similar. it does take about 5 seconds to work on the desktop, so that made me think its probably a bit overkill for a mobile project.
After Effects:

So I scratched that and decided to use steiner points as @obidobi suggested, so now the task was to figure out where to place the steiner points.
A good visual example of how steiner points work is with this web demo http://javascript.poly2tri.googlecode.com/hg/index.html
I am currently generating a grid of points based on the bounds of the mesh, then I check if they are inside or outside the shape, and delete the ones that are outside.
This leaves me with this (points being shown with spheres)
Then I factor in that point data as steiner points to get this as the final!
Yes, there is room for improvement, but this is good enough for now.
As someone who spends most of his time in JS, there was a good learning curve here of how to get this all set up and working. At the end of this (after I get further in my project and make sure this battle tested) I will put up a nice happy Poly2Tri repo for Unity that is easy to integrate into projects and can be called with 1 line from C# and JS.