I wrote a script that does this...but unfortunately it's for Unity. So if by some crazy coincidence you're working in Unity, I could share it with you.
So you want it to automatically reconnect the remaining verts at the end of a loop upon its removal? Yea, that's something that's going to need to be scripted.
That looks absolutely amazing, that it's presumably not a scripted sequence and all dynamic is just mind boggling, I cannot wait to get my hands on this.