Thanks ladies! I started the wi/wo method early last week and it's been working...we are on night 6 tonight & he's slept right through two of the nights.
I can't say we really ever sleep trained him. He has always slept on his own and then in his crib in his room from 8 weeks, onward. Eventually he was great - he went to bed with no protest, didn't have to do anything more than milk and then in his crib. He has his own soothing techniques - asides from his soother.
He'd wake up the amount of times you'd expect for the age and then around 10 months or so, he regressed hard. Waking multiples times, some times hourly. Screaming at bed time, etc, etc, etc...
The only thing I'm wondering now is will he only get back to getting to sleep on his own OK but still waking multiple times, needing out help to fall back to sleep? I wanted to eliminate that to begin with and we ended up in a storm of sleep hell LOL