I think I know about the item taking two slots, I have it on the list of things to resolve.
As for the sleep, the character should have woken up. There was a bug related to skill usage (maybe Owlking or Magnus skills didn't woke you) which is now resolved, but might have not been deployed. Another issue that might have caused this was "rest until full health" action, which will be resolved in the next version also. It moved the time forward too fast and even though the stop happened, it was probably too slow.
As for the things stopping this seems new, could you tell me more about what happened? Were you able to move cursor and yellow border of the tile, take any actions other than sleep, open any windows or was the game completely unresponsive?
Thanks for detailed explanation and screenshot!