First thing's first, here's a picture of what healthy living roots on an orchid looks like:
http://www.aboutorchids.com/blog/wp-...ts_1_640px.jpg
Here's a brief video on orchid roots:
Understand Orchid Roots: Discover & Appreciate Orchids | eHow.com
Damaged roots tend to delay an orchid's bloom cycle and adversely affects the health of the plant, this is why I put special emphasis on the roots first.
1. I
highly recommend repotting to a pot that actually has
real drainage holes.
A pot with no drainage holes, is bad news for an orchid's roots.
If you look at the photo of the Dendrobiums growing in the wild, you'll see just how much air the roots are receiving. It's
a lot.
My potted Dendrobiums are all potted in pots with drainage holes.
I also have Dendrobiums mounted onto pieces of wood with nothing but the wood itself, left hanging outdoors. The roots are lookin' real good on these even with all that air.
My thoughts are that a 1" drainage space on the bottom of the pot is not good enough, the water will drain down there and settle in there like it does with a septic tank. If you don't actively go and drain the water everyday, that
stagnant water is going to go bad very fast. That
bacteria and fungus infested water will instantly kill off any living roots on your orchid within days.
2. I think you're going to have to dig in there and do some investigating of whether your plant has any living roots on it anyways based off of what you told me and what I had just said above.
Your pictures while very clear
does not show whether the Dendrobium has roots or not. It is very difficult to make an accurate assessment about your plant without knowing without a doubt that your plant's roots are alive and intact.
My assessment of your situation is, you're going to have to take that plant out of it's pot whether you want to or not, and whether the plant likes it or not, or that thing has a very low chance of survival anyways.
It
will not die because you removed it from it's pot to check on the health of its roots.
Just because the previous Dendrobium died within 3 months
under your care, only means that it had about 3 months of life left
when you purchased it.
It could've been rootless and about to die at the place you bought it from for several weeks to several months already. It could've been rootless and about to die at the wholesale nursery for months already, who knows. I had a rootless Dendrobium last for 6 months or so.
3. It is still too big.
You will not risk breaking any roots "by shoving it into a smaller pot". The pot only needs to be a snug fit for the root mass, not much smaller where you're having a great deal of trouble getting the plant's roots in there.