I was writing a huge reply the other day, and the browser closed on me, I was pissed Well, here goes a short summarizing:
1 - Rohan is biiiig, so let's assume from Edoras (its capital) to Bree. I would say one month on horseback, on a standard pace, without extraordinary perils on the road, like those faced by the fellowship. That is, taking into account that the distance would be around 1000km, through the Greenway. I might be wrong about that.
2 - The biggest Roleplay problem in LOTRO is the "mary-sue" issue. Maaany characters (specially on Landroval) have background stories such as close interaction with canon characters, fighting once against Sauron, having a major importance in the recent events of Middle Earth, etc... Now imagine that there should be hundreds of active roleplayers in the server, imagine if all of them personally received a "mission" from Gandalf or Strider, for example? Gods, then these guys should hire secretaries, to handle such amount of acquaintances and "secret" agents. Tying your own story to the quest storyline is a very nice idea, but try to steer away from personal interaction with canon characters or any role in the main happenings of Middle Earth, is my advice