I didn't read everything, but I did read most of what was said. Alot of it is trial and error and learning your water habits. Of course I'm speaking with the information you gave us, but this could apply to almost any beginner.
I live in Colorado, and I'm a classic fussy-er. I admit it lol It's been dry and hot here. So, with that knowledge here is what I do...
For me, what I do is get them out of that moss, trim any dead (only black, squishy roots) and repot in pre-soaked bark. I do not use any chemicals as the plant I bought hopefully has minimal to no signs of rot, at least bad enough to use any chemicals.
For me, the plastic pots just do NOT work. I don't know why. It may have something to do with my watering habits or my fussyness over wanting to check the roots all time. Plain terra-cotta pots from Home Depot are what I use and they do great.
Mine have always always had a 3-4 month period where they look like they're declining. The lower leaves get wrinkled, the roots may turn brown (but NOT squishy). After the few months I see new leaves coming and green roots poking out of the brown ones. But it does take a few months of wondering if it's doing ok.
For the aerial roots that dry out before the ones in the middle, I take a squirt bottle and just dribble water on the aerial ones that are silver. This way the middle can still dry out properly and the aerial ones think it's more humid than it is.
Again, I'm sorry if this has been repeated, but hopefully you can find your groove for you and your orchids. Some orchids take longer than others to bounce back, but for me I have to get it out of that moss or rot will occur. So I don't know about that whole, repotting slowly over the course of a couple years.
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