What I'd like to know is that, when your trying to stay hidden jumping into a system. I know it's possible to try to conceal your approach by using celestial bodies to cover your signature
If there's a proper early detection system in the network (which would consist of satellites in solar orbits), it's not easy to hide a jump behind a planet. There will be satellites to the sides of the planet and probably further out in the system.
Also, as noted in Strategic Operations, the handful of valid pirate points in a star system are primary targets for early warning satellites.
But if someone chose to come in closer and lets say they jumped in using a planet as cover and miscalculated, besides the obvious colision / gravity threats, would the jump wake have a chance of bouncing off the planet and hitting the Jumpship?
Sure. Would it do anything? No. It's a flash of light and radio waves.
The fancy space-rippling effects of an arriving/departing JumpShip will not reflect.
It would seem to me that if another ship was caught in your wake, that you could get cuaght in your own.
Only in one circumstance is that a problem: if your arrival point is within 27 kilometers of your departure point. Yes, JumpShips can make jumps that short.