Situation 1. A bird in the hand is worth 2 in the bush and that tom has the hens so you are in a loosing battle from the start if you are not at/on his level when he flies down. Try to get up to that ridge and set up on his level in the dark and see what you can do right at flydown. Call to the hens if need be, but if you aren't where they are and he wants to be well...
Situation 2. Yes, try some more agressive calling. you might just fire him up, but again, if you aren't where he wants to be your screwed again. The best caller in the world can't pull a gobbler to where he doesn't want to go, period. Your location should be your VERY FIRST CONCERN. Calling is secondary.