It should matter.
A player should take responsibility for their decisions. If they want to drop out close and accept the risk them they are free to do so. It's that acceptance of risk that's the absolutely critical part.
There is risk in this game, real risk that you can make a poor decision and lose everything, especially if you have not provided yourself with a contingency plan.
All it takes is a little planning and understanding of how things work, and just like life you can make your way through it in a largely low risk manner and not lose all your hard work in a moment of thoughtlessness..
No, it should not matter, for both gameplay reasons and immersion reasons:
Gameplay: You are prompted with "Safe Disengage" and as such you should be able to disengage safely, after all that is what it says on the tin. Also, as the angle you approach the station does not seem to match the angle you emerge from SC and are relative to the station there is a massive slice of pot luck involved - again, "Safe Disengage" shows no matter what angle you approach the station, this would not show if it were not "safe" to approach from the rear.
Immersion: You jump in from Super Cruise in a Type 9 fully laden with Explosives. You emerge from SC inside the walls of the station and you should go "BOOOOM!" rather impressively - no more station, no more ship, no more pilot, no more other ships, no more commodities, no more anything at that location. The fact this doesn't happen really doesn't make sense. Once you factor in all the occasions this happens then you end up with a rather sparse galaxy, and Orbis Stations would no longer be built due to this rather shocking vulnerability.
Dropping in facing the rear of the station and having to react fast to avoid collision, or even being unable to react and ploughing headlong into the exterior - that's fine and is the reward for the risk the pilot takes jumping in from that angle. Dropping in and finding yourself embedded in the walls? It's a bug, and should be ticketed.