I'm inclined to be fairly liberal with it, too. While it's good for the rules to have features that keep people from doing something cool every round of combat (otherwise, the game gets ridiculous), it's most fun to be able to really do your thang in each round, instead of spending your entire combat action moving into position. Any rules interpretation that facilitates this is a good thing IMO. Let the good guys and bad guys spend as much time as possible actually fighting, and as little time as possible making double-moves.
(Requiring skill-checks to maneuver is fine: even if they fail, at least the player got to roll a die during that round!)
Daniel