Say there is an equilibrium of creatures currently in play and I control Oath of Druids. It is now the beginning of my upkeep and I have an untapped Orchard. How do I declare the stacking effects of Oath, if possible, to put a token into play under my opponent's control in order to Oath this turn?
In this situation, Oath will not trigger. Because Oath has a conditional trigger, the condition has to be true when the ability could trigger in order for it to trigger.
My opponent has Tolarian Academy in play. May he/she respond to me playing my own Academy by tapping it for mana? Since playing lands does not use the stack I am confused as to whether the opponent can respond to the land drop that will kill both of them.
Your opponent could not use Tolarian Academy for mana. Both go to the graveyard before either of you can play any abilities or spells.
Along the same lines, I play tinker and my opponent has some lands in play. I get a Sundering Titan that kills the lands. Can the opponent respond to the Titan effect by tapping for mana or must they respond by floating mana in response to Tinker if they are going to respond at all?
Your opponent could tap his lands in response to the Sundering Titan coming into play. Its ability does use the stack and can be responded to like any other ability (note: your opponent could always choose untapped lands when the ability resolves and you wouldn't be able to tap them for mana)
Can I get the mana from Mana Drain if I counter a instant or sorcery cast off Boseiju?
While the original instant or sorcery will not be countered, the addition of mana from Mana Drain is not dependent on this. So, you would get mana at the beginning of your next main phase.