We go through several months of dry conditions here in Florida. But even in the wet part of the summer I still water at least twice a day. When it is really hot I can water three times a day. They are under a roof and not out in the weather.
I'm on my way to eliminating all wooden baskets and hanging just on wire. It works for me as part of thrip control. I still have a several dozen to go to get them all out of baskets. But as the baskets deteriorate I'm happy.
The one thing I've noticed that people talk about are roots and how to control them. They are vandas. If you are going to grow and grow them well then you are going to have to realize that you are always going to have a massive amount of roots hanging down. That is the nature of the plant. You are always going to have to weave yourself around them where you have them situated. My shadehouse is about 8.5 high and the roots of many of mine hang to the ground. There is no controlling that.