Warpiglet-7
Lord of the depths
I am going to make a mock up with sadistic orcs chasing a party and use my table with minis for relative positioning and see how it looks.It's similar in structure to 4E's skill challenges except that I'm tracking results as a contest. I don't necessarily think in terms of distance, but instead in terms of success totals or averages for a group. Sort of. A lot of times it just comes down to pacing and fun. I also use a similar structure, a set of connected skill checks, for things like escaping collapsing buildings, complex traps and what not.
It helps to just do it, of course. I also like to think ahead a bit if I think it's a possibility and jot down some potential obstacles sides could either use to obstruct or avoid. Also, are there any shortcuts, can you run through a building or alleyway instead of around.
The DM's version of obstacles in the chase rules is pretty limited, in particular it doesn't talk about using the environment to slow down your pursuers. I generally make my own obstacles up on the fly or have a little bit figured out ahead. Add in my list of PC skill proficiencies and it's off to the races so to speak.
I realizes some is theater of the mind