Some people keep Jack Dempsey's and Oscars together and have no problems, other times aggression rears its ugly head. It's either going to go one way or another. Obviously the larger tank you have, the better it will be because the fish wouldn't be crammed together all the time. I think it would be up to you to decide whether there is too much aggression when the Jack Dempsey is in with the Oscars.
Regarding the Oscars pairing off, I'm afraid you've got a very long wait. Contrary to what some people say, Oscars do not pair off at a very young age. Yes they hang around with each other but you will not know you have a proper breeding pair until they hit maturity and start laying eggs. If you had a batch of six and you did notice that two were hanging around with each other, you could take the chance and remove those two and hope for the best, but it wouldn't be conclusive evidence I'm afraid.