Loremaster of Outland

Two words: Quest text.

Reading it might just save you a lot of searching WoWHead :P

So you've decided to try and get Loremaster?

Addons you'll want to help you along the way:
1st is EveryQuest. A helpful tool that utilizes the recent quest database functionality introduced to the game, allowing you to see which quests you have not completed, in every zone/ dungeon / raid. It can also filter out various quests you might not want to start ie; raid specific quests / cooking / class etc.

The 2nd is Lightheaded which has the ability to show you valuable WoWhead comments and info when you access your quest log. It can also show you where quest givers are in the form of coordinates. Very very helpful. Also displays quest chains (very helpful) and helps you find where you are up to in that chain.

The 3rd is TomTom waypoint arrow. This will integrate with your EveryQuest & Lightheaded and allow you to see where you need to be on the map, mini map and on screen HUD. Its a small movable arrow that points the way to objectives and/or quest givers and any other location you wish to ask it to point to.
For instance, if you're currently looking for a druid in Moonglade named Rukthaan (fictional as I can't think of any of their names right now) you would only need to type the NPCs name into Lighthead's search engine. Find the right NPC and then click on the provided coords inside Lighthead interface, that will automatically engage TomTom's way point arrow to help you locate the NPC.

But that was a hypothetical and EveryQuest should tell you exactly what quests you need to complete in order to finish each zone as you go on. It will also have the functionality to help you see which quest givers have what, and allow TomTom to tell you where to go to find them. But.. incase you want to trek to a specific NPC and want info on the (what could be) thousands of quests you have remaining you'll want Lightheaded as well.

I've done Loremaster Kalimdor, Eastern Kingdoms, Outland, and a third of Northrend, also all of Cataclysm with an earlier alt. Outland is the hardest. Kalimdor, EK and Cata have easy to follow pathways that as long as you do the expected order of regions and quest hubs in the regions, you will get through with no major hassle. The parts of Northrend I've done so far seems similar. Only Loremaster of Outland feels all over the place.

First, soloing the other continents is reasonable; with Outland it's very difficult. I started Outland at 60th level and finished it at 82nd! I started doing almost all the quests necessary for Hellfire, but I couldn't complete without doing group quests. And tough ones to solo. This was a surprise, as I could always do enough quests in Kalimdor and Eastern Kingdoms solo. I prefer working that way so I decided to move on to Zangarmarsh and come back, rather than getting a group together. I worked through Zangarmarsh fairly easily and did most of Nagrand out of order before Terokkar. Couldn't finish Nagrand. Still had quests missing and group quests I couldn't do yet. But at least by this time, I could go back and finish Hellfire. And so it went on.

You are not only expected to do two and three man group quests, in some regions these are 5-man quests, and rightly labelled. There are even dungeons that count! About halfway though Outland, I went on to Northrend and did Howling and Borean, which took me to 75th level. Surely you'd think I could come back and finish Outland now. But no. I worked my way up to 78th, taking on most of Blade's, all of Terokkar and Netherstorm, then most of Shadowmoon; but still I was blocked and needed help to get to the final section of Shadowmoon. I only needed help with one quest to get through but I still had a set of quests left in Blade's that I thought would be easy, the Ogrilla ones. And so they were, easy, until I only needed six. At this point I had only 5-groupers and dailies left. Rather than get help, which I probably should have, I decide to level even more, and did most of Icecrown and Hyjal, taking me to level 82. I was gonna spank those half-dozen Outland 5-groupers! And mostly I did. But even then there was one I still had problems with. Not because I died, nothing can touch you in Outland if you have Cata greens and blues, but I couldn't be in enough places at once. So even at 82nd level, I had to get help from a couple of 66th level guildies who were in the area.

The second reason Outland is tough is that it's not quite in order. For example, you can't finish Nagrand before starting Shadowmoon, because there are quest chains that move from region to region. Not just breadcrumb ones, either.

Third, it's tough because for some regions it's very tight. You can't choose to miss too many quests in Blade's or Nagrand; you need most of them.

Finally you need to make choices on the breadcrumb quests. For example to get to Netherstorm you have a whole set of mutually exclusive choices of breadcrumb quests to make, each counting for different things. So you have to be on your toes to give yourself the best chance.

No wonder you keep reading that people do this part of Loremaster last. Good luck to all of you doing it. Don't expect this continent to be easy to finish if you are trying it at 60-70th level.