Definitely agreeing with alice and ES on their comments there.
There really appears to be rot among there, like stem rot.
JJC - your pot looks quite ok there. Not sure what the condition is on that last leaf, as I can't see for sure if the region that connects the leaf to the stem is changing colour - becoming off-colour or whitish etc.
For the latest photo, the media is now looking ultra dry.
In any case .... this particular experience with the plant's health issues can be used to advantage.
Assuming you have nice growing temperature range, and nice lighting level ....... your potting method appears to be ok. And assuming your watering schedule was ok too ------ ie. not overly wet or soggy roots most of the time ..... then make sure to consider whether or not your orchid gets at least adequate (but not necessarily constant) gentle air-movement. The gentle air-movement can definitely help cut down or eliminate rot issues.
Although - if by chance your media was overly wet most of the time ----- leading to root oxygen starvation and then root rotting, just try out one method of watering. Just try it for a little while - not just on this orchid, but any orchid ------ see the attached pic ..... use a spray nozzle and spray lots of water in the band shown. Spray enough water so that the water gets well into the media, and really wets the media ---- all the way down the sides.
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