There is no proof that will ever satisfy a person dead-set against this. Ever since I brought this home from school as a child, my whole family ribbed me mercilessly for it. If you tell a person that 3/6 = 1/2, they'll believe you - because they have been taught from an early age that fractions can have multiple "representations" for the same underlying amount. People mistakenly believe that decimal numbers don't hav…
In the real numbers, which are not always simple or intuitive, 0.99... = 1. That's true and I seem to understand the proof.
But the real numbers aren't the only system that might be sitting behind "0.99..." and "1" when I write those symbols down and talk intuitively to people in my family. The reals are just the system we're taught first.
I believe there are other systems (I think the surreals are an example) that work just as well for everyday purposes, but where ( my understanding is that) there are numbers that differ from 1 by a value that approaches zero, yet those numbers are not equal to 1. (I've played with the surreals but only as a hobbyist.)
If you do calculus in these other numbers, I think physically meaningful problems will still yield the same answers. (For example Zeno's Paradoxes are still not an excuse for failure to attend school.) But it isn't a law of nature, I think, that all number systems that can hold 0.999... and 1 must make them equal.