I feel like a good rule of thumb is the eye ends up about halfway between the size of the inner and outer when the process begins. Just from observing these happen and being rather fascinated by the process. Also I've noticed there's often a stubborn little bit of the original eyewall left that takes a while to die.
The EWRC seems to be moving along fairly quickly. This is not shocking as it is moving over extremely warm water and seems to be dealing with fairly minimal shear atm.
Looks like a classic EWRC to me. This one may take some time due to the large size of the outer eyewall. Hard to say if it will have time to recover by the time it makes landfall.
The closest analogue we have is estimated to cause 75 billion in damage (based on a study in 2018) and last time this occured, the entire island of fort Myers beach was under 3-6 ft of water:
https://en.m.wikipedia.org/wiki/1944_Cuba–Florida_hurricane
Ian is about halfway across Cuba and seems to be holding up well this far, although it is just now getting to the higher terrain (about 1,500 ft hills)
Yeah, sometime winds take a while to respond to improvemants on structure, but I suspect by the time they make the first pass, it will be at least 85 kts