Knowing When to Water

The only house plants I have indoors are a Spathephyllum, a Pothos and 3 Orchids. When the Peace Lily starts to droop I water them all. I take them outside and let water run through the pots and drain before bringing them in again.

The only Orchid that I don't water outside is the one in a tall glass cylinder. Once in a while I take it outside, flood the pebbles in the bottom with water and then turn it on its side and let the water run out.

Last year's bloom.

I keep thinking about taking it out of the glass container and repotting in a regular orchid pot in orchid medium. I wonder if after all these years of confinement it might die of shock? Or would it take hold and start to grow?