Just to know, there are 3000 or so species of "Orchid." The orchid you have is a Phalenopsis. Phals are given the branding that they are somehow an easy or beginner orchid. I pretty much killed every one of them I had at the beginning, for the same reason as you say, because of overwatering. After a lot of reading, I realized that phals, and cattleyas and many other types of orchids are really a lot like cactus, so I went and bought an inexpensive epiphitic cactus. Reason? When the Cactus gets watered, the Phals get watered.
It really helps to understand that these are "desert" plants, in that they are growing on trees, and touched by mist or rain a bit every day. But otherwise, they are "dry." This may take a while to soak in. I know I was about ready to quit for at least 2 years until I truly understood the meaning of the word desert plant. So, what happens to a cactus if it is soaking in a bucket of water? It quickly rots and dies. What happens to an orchid (other than Phrags, and some Bulbos and other hydrophilliac orchids) well, it rots and dies. If the roots are in the water, they rot and die, if the leaves are, they rot and die.
Watering them every day is not a problem. The problem is draining the water away from the root, which is what does not happen in an enclosed environment. If you have the Phal mounted, on a stick with no moss around it, you could water all day every day. In their wild state many epiphitic orchids are rained on or misted on at least part of the year.
When your orchid is in a flower pot, the time that it takes to dry out is your "clock" for when you should water. This will depend on your ambient environment, so no one, unless it is someone on your own street, can really give perfect instructions for "when to water." The skewer (or chop-stick) method is used a lot.
I would say take the plastic off. Phals in super markets usually come from Taiwan or China, and they need that plastic wrap type cup on them because they are in a shipping container and will not be watered in a while. The plastic keeps the roots from drying out. Chunky bark is best for Phals. Other orchids use small bark or other types of potting medium.
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