A satellite can stay in pretty much any orbit, LEO satellites are pretty common. The lower the orbit the more air particles slowing the satellite down and the more need for readjusting it either by its own engines or by a spacecraft.
Now for a human skydiving, there is really no limit. It's just the matter of drawing a line between a suit and a capsule; if the suit can provide arbitrary amount of air, shield from vacuum, dissipate extreme heat of passing through the atmosphere and so on, there is no limit. If it can't provide arbitrary degree of that, there will always be a slightly better suit allowing for a slightly higher jump. No "top height" as such. Current 39km is the result of a golden middle between marketing value of the jump and cost of equipment and research necessary to perform it.
On orbital altitudes, the vehicle the jump is performed from would have to move in such a direction and speed as to provide optimal entry curve instead of just dropping the person into the orbit and leaving them there to orbit Earth forever. But other than that, there is no reason why a man couldn't be lobbed from behind Jupiter, make a slow-down loop around the Moon, then spiral down to Earth... given some marvelous suit that will withstand the atmospheric entry.