Oscars and Jack Dempseys are both at about the same "skill" level. If you keep them fed and keep their water clean, they'll be perfectly content. I have read that Oscars can be a tiny bit more sensitive to water condition, but I don't know if this is true or not. I will tell you that I probably fall somewhere in the middle in regards to water quality (could be better, could be worse) and maintenance habits, and mine appear healthy and show great color.
Perhaps a bit off the subject, but important to know, is that varying these fishes diet is almost as important as keeping their water clean. They can live on cichlid pellets alone, but mixing in flakes, freeze dried treats (worms, crickets), veggies, etc. will promote better coloring and general happiness.
Both of these fish are very owner-responsive, and each can be quite colorful. You won't go wrong with either. Again, good luck!
-sj