I traveled Colorado last year on a downhill longboard, I would stash my pack and bomb hills in the mountains. I can give you some good pros and cons from my experience.
Pros- increased mobility, I found myself going into places I normally wouldn't because I could get around quicker, like Denver. Great way to meet local skaters. And there's nothing like cruising into the sunset on gentle rolling hills.
Cons- you gotta be careful man! I had a 45 pound pack and had a nasty fall. I was in boulder coming down the hill from the park on the west side of town, got a bit too much speed for the weight I was carrying and hit a small pebble that sent me flying face first to he ground. I had to skate to the hospital to stitch my lip up (they wanted to charge me $1500 for two sutures and ten minutes of the doctors time), broke a rib, sprained wrist, and two chipped teeth.
Some cops won't like you either, I got a ticket for skating down the sidewalk in downtown Denver on the street with the strip mall(6th street maybe?) after some research into this cop for the harassment he gave me, he is known to harass homeless and travelers coming through that area.
I would say the pros outweigh the cons but be careful, don't bomb hills with a 45 pound pack and just cruise.