Here is my setup:
Slim 250GB XBOX 360
2 Official Xbox 360 Controllers
1 Charge and Play Pack powered controller (primary controller)
1 Battery Operated (secondary controller)
1 Wireless Headset.
I first started noticing this while watching netflix a few weeks ago. The controller would time out after a while and shut itself off like normal. Then when I go to turn it back on (hold the xbox button) it does not connect to the xbox. The lights just keep blinking and the xbox does nothing. Sometimes but not all the time while the first controller is blinking and trying to connect the second controller will connect for me if I try to turning it on. This does not happen every time though. The other times it will just blink just like the first one. I just noticed as well that my headset does the same thing. It occasionally does it during games but I don't often have my game paused long enough for my controllers to time out. In order to get anything to connect again i have to hit the power button on the console itself then restart the console. It's such a pain to do that every time because then I loose game progress or I have to go all the way back into netflix. I'm not sure if it is my console or something I'm doing wrong any help would be great. Distance should not be a problem because I Sit like 2 and a half feet away from my Xbox.
I don't know if this is a related problem or not but my primary controller will sometimes vibrate like normal during game-play but will just keep vibrating until i power cycle my xbox. I'm not sure If the secondary controller does this or not I don't use it enough to know. I suspect this vibrating problem might be a sign of the play and charge pack going out. the pack is kind of old.
Before you even suggest it: YES, I HAVE TRIED THE SYNC BUTTON ON THE CONSOLE AND CONTROLLER.