I want nice pseudobulbs! Should I repot again? Dendrobium Red Emporer Prince

[aemiklain]

I bought this guy this spring in bloom and was rewarded with 3 new growths after too! It came in a 5" pot with medium bark, which I thought was a bit too big a pot. I repotted in a 4" with fine bark mix when the pseudobulbs started to shrivel up. The new growths put out loads of new roots and were doing great, the old growths were much plumper for the last month but now seem to have regressed a bit and the leaves are starting to fall now, I like the windows open and it may have been in the 50s recently so i assume thats why. My question is, this bark I use is wonderful for overwaterers because it doesn't retain moisture as long, I like to soak my orchids about every 5 days(I'm in Minnesota so we have quite a variety in the climate deparment and it's starting to get colder. I've noticed when it's time to water this is the only pot that still has plenty of moisture in it, so I'm wondering if I should move up to a medium size bark so it's not so wet constantly. Wondering if I'm having some root issues, they don't seem as white and lively for the last month. Any ideas? Another question, do new blooms form on previously bloomed canes or just new growth?