a male jack dempsey would definately not work since they get very large 8-12inches, and are very agressive. and a female gets anywhere from 4-7 inches.
Since he is already 5" I think that limits your options to just him. If he was smaller I would say two if you REALLY keep up with water changes.
How does a 90 for two make sense if a 75 is too small? It is 4" taller and only 15 gallons larger. If it was longer I could understand, but as far as they are concerned it is not much bigger at all. If a 90 is fine then so is a 75.