The time we actually know what money they would make, making it concrete for tax, is when they sell. And we already do this.
No it's not. Most people don't pay capital gains because things like houses don't have capital gains applied. I.e. the rules are set up so that most people avoid capital gains tax when they gain capital. Everyone pays income tax with the same rules, and some people pay capital gains tax as well if their risks pay off. We tax the profits and let investors absorb the losses.