My point exactly.
He knew it would have a finite duration. He's an intelligent guy. Is it that unreasonable to assume it might have occurred to him, during eight hours of nigh-terminal boredom, that a more long-term solution would be needed at some point? And having thought that far...
See above. What do you imagine he thought Vaarsuvius was planning to do when she was restored? Loot the dragon's hoard and walk away, leaving its righteous vengeance contained only by a spell that was just about to run out?
He could talk to Vaarsuvius just fine - the dragon would only have to translate V's replies. And for Roy to reason that "the dragon might break free of the suggestion if V mentions that she intends to kill him" - would require Roy to suspect that V, in fact, did intend to kill him. As well as assuming that V was incapable of communicating with him without cluing in the dragon.
"What are we going to do about the dragon?"
"I was thinking along the lines of what Elan did with Dorukan's dungeon."
This one, I have to grant you. But it just brings us back to proposition 1: that Roy didn't really care what happened to the dragon, so long as the OOTS weren't on its menu.
And I suspect you have a vested interest in reaching a "Vaarsuvius's instinctive alignment is Thoughtless Evil" conclusion. But even if we were both right - what difference would that make?