Am I watering it correctly?

[NYCorchidman]

These are tough because the area they come from naturally (Far East Asia) have nearly freezing winter, boiling hot summer with monsoon, then super dry spring and fall (but occasional rain of course and these are usually found growing right by the ocean, so the air is usually quite humid even when there is no rain).
Yet, it is always of course best to give them good condition as much as possible to keep them happy and flourishing.

I have way too many plants now and watering (as much as I love tending my plants) has become a major work for me.
Unfortunately, it is such a hard thing to get rid of healthy plants that I like. so I am rather puzzled at the moment.