Another friend of the same era (i.e. early 1992) has been here forever on various passes - he's never bothered with PR. I've been a PR since 94 and honestly I don't see any real difference between the benefits I've supposedly enjoyed - I have CPF but he has savings; I have medical coverage but he has medical insurance; my child goes to a local school but so do his (they are SC); we both have transitioned jobs many times without any visa issues of note. I had a HDB once for about 3 years and that's the only difference - we now both own condos.
Personally - if I could wind back the clock I wouldn't bother with PR.