Grocery store Orchid in pot w/o drainage

[Stelios369]

I've killed almost every orchid Ive ever purchased. Usually it's b/c I water them too much. About 18 months ago I bought one of those mini orchids that suggests watering with one ice cube each week. The roots are in a plastic cup with a hole in the bottom. That cup sits in a pot w/o any holes. Amazingly that little guy has gone thru 4-5 blooms w/o any issues.
Once again, I thought I'd try a larger orchid. This one didn't come in the typical plastic cup with peat moss, etc. This one came in a pot without any holes in it. The roots are packed with [the stuff that looks like brown wood chips] and that's it! It's hard to know when the plant is ready to be watered if I can't pull the cup out to check. W/o drainage holes there could be a puddle of water down there and I would never know it.
I was told not to repot the orchid right away when I got home. Does anyone agree with that in this case? In terms of watering- my best idea is to water the plant, and after a few minutes pour all the water out. Then repeat the pour until I'm sure no water is sitting at the bottom.
Orchids are really f**king expensive, even from the supermarket. I want to keep this one alive at least until it's second bloom. Does anyone suggest any tips? I was a bit shocked when I didn't see the roots in the plastic cup with peat moss. Don't orchid roots like to be somewhat compact?
Finally, the ice cube idea has never worked for me!