a lot of it is based upon gut instinct.
if i'm humming with my putts, i will run nearly everything inside 100' w/ a putt/jump putt unless the wind is just brutal.
if i'm off on my putting, i'll generally try to pin everything outside 50'.
as for the tweeners, it is a constant judgement call.
if there is a dropoff behind the basket, it is best usually to lay up.
also, i try and leave myself favorable situations. if there is a dropoff behind the basket, i will try to end up pin high and on the right side, which leaves me a straight on look with no fear if i'm pin high, and a hyzer putt that will fade and stay up if i'm a little bit short. similarly, if there is a headwind and no danger behind, i will try to slightly overthrow the approach so i can have a tailwind coming back.
course management is key. i havne't had an insane putting round in about 6 months (went 17 for 18 on first putts inside 70', with my only miss being a 65' uphill jump putt that cut through and bounced off the pole), so it's been a while since i've had seemingly reckless abandon with my putting game (usually i'm more like 13-15 out of 18 on first putts).
one thing i will do is to use a knife hyzer jump putt on some that are outside my range and just try and pin it.