For me, the best way to solve this, is to make it really easy to change between one and the other, at least at the beginning when that's the only state and there is not much code yet.
Start with the easy, and change it when you need it.
If you use the easy boolean, but your code requires a different class for each layer with that boolean (I'm looking at you DDD) if you need to change to an enum...good luck touching everything.
If you start with the complex enum, thinking that the boolean will need to change, then you'll realize that you don't need an enum or a boolean, but a string, and all that extra complexity is now in the way.
Boolean or enum, doesn't really matter, but make it so that you can change it as easily as possible, if needed
Start with the easy, and change it when you need it.
If you use the easy boolean, but your code requires a different class for each layer with that boolean (I'm looking at you DDD) if you need to change to an enum...good luck touching everything.
If you start with the complex enum, thinking that the boolean will need to change, then you'll realize that you don't need an enum or a boolean, but a string, and all that extra complexity is now in the way.
Boolean or enum, doesn't really matter, but make it so that you can change it as easily as possible, if needed