All the replies so far have focused on why it might be realistic, in a Medieval setting, to have high travel Obs. Fine. Sure. I’m personally more concerned about playing the game than simulating reality.
And what bothers me is how difficult it is for someone just starting out in Riding (typical Will = 4, so starting Ride = 2) to get the Routine tests he needs to advance that skill. With a minimum Ob of 3 (Nearby +1, Roads +1, No hurry +0, Horse +1), our newbie needs to somehow raise 5 dice to get a Routine test. There are no listed FoRKs for Riding. You get +1D for reins and saddle. You can get +1 Helping die, but only assuming you have friends on this trip who also have the skill. I’m not saying it’s impossible—a linked test might generate a fifth die—but it’s awfully close to impossible if you don’t have friends available for a helping die. And it really IS impossible if you’re weak-willed (Will 3, Riding 1).
If the minimum Ob for travel were 2, then the problem goes away. Then our Tyro would only need 3 dice for a Routine test, and that requires nothing more than reins and a saddle. Maybe that’s too easy? But better too easy to advance than impossible. The GM can always say Yes if he thinks the players are test-mongering—or insist that this section of road is in bad repair. So in short my fix would be to revise the Obs listed for Terrain: “Good roads (+0 Ob), bad roads (+1 Ob), fields etc.”
Maybe I’m missing something here. In other cases like Persuasion, there’s a trick to generating Routine tests: get into a Duel of Wits or a Bloody Versus. But I don’t see a similar option available with Riding. It’s HARD to ride in Fight or Range and Cover—and rightly so. To attain that level of mastery, you need to do a lot of travel. And the Obs for travel work well enough once you’ve advanced Riding to 4. But below that (and 4 is a pretty high starting skill exponent!) it seems like you’re stuck.
Thoughts?