Cool. Thanks for the replies. So it sounds like under normal circumstances neither side is likely to get the jump on the other, unless they are specifically attempting to be stealthy and are moving very slowly. That makes sense
Here is the next scenario I had in mind:
Scenario 2:
The group's rogue quietly moves up ahead and peers into the next room. An enemy is standing there in normal light, but facing away (out of line of sight) and not paying attention to the door. The rogue moves 2 squares in, makes a stealth check, and attempts to move towards the enemy to sneak attack him.
Question:
The PHB states that in order to maintain stealth you must have
some degree of cover (low lighting or foliage?). In this case though, supposing that the enemy does not bother to turn around and check his back, could the rogue sneak up on him and make a surprise attack? Would his stealth be automatically maintained without the need for any additional checks, even if he has to cross 10 squares (two at a time) to get to the enemy?
Or is sneaking up behind an enemy much more difficult?