To circumcise or not to circumcise?

[Tiberius]

It gets much more loose over time though, and the more you retract it (especially when you pee / masturbate) the easier it will become.

In fact, this is the kind of advice that should be given by parents and doctors to all boys (for peeing at least), to reduce the likelihood of ending up with phimosis.

Yup, but I peed for years without retracting my foreskin, no problem. Its not an issue if the foreskin can't retract, because that means its still attached to the glans, so there's nowhere for bacteria to grow.

Now, if the boy / man is having issues peeing, i.e. the foreskin is so tight it hurts to pee, then circumcision might be the only option.