My throw in.
I would suggest if you're going to go about the Student/Teacher approach with an apprentice that you should take a good deal of time and draw out everything that has to do with your characters ability in the specific trade. An example is following;
Lancastor Swiftnettle, my primary character is a merchant. He is also a criminal. He has been masked for over two years and manages to be successful in his field. Why? Because he(I) knows how to do his trade exceptionally well. Can I just say that? Sure. However to sell it I need to prove it time and again. Does anyone know he's a criminal? Nearly none. But everyone knows he is a merchant. And a rude unsavory fellow. Also, why does no one know he's the wanted criminal? Goes by the name Lan; a common name like Bill or Jack. Back on subject: You want to be Master you need to be able to teach Pupil. Are you teaching bout swinging a sword, archery, horsemanship and mounted combat, or are you going to be laboring with the person over a forge, in the kitchen, with needle and spool, or are you like Lan; selling things?
Next: Can you teach it in detail to where it's interactive, in-depth, and even more difficult; kept interesting and fun? If not, then spend a little time looking things up on the internet. Youtube has just bout everything for learning even older stuff that'd be in Lord of the Rings time period(Medieval times.) So you have the tools if you don't have the know-how presently. Just put the time in.
How will you teach and what will you teach when and so forth?
Landroval is an excellent place as any, but; No I am not an elitist, but I do enjoy the quality just as I do enjoy the quantity. If things are a jumble and messy it can become a headache and you or the other(s) will lose interest. Just like Kinships, and i've founded and lead plenty that have flopped. Same with teaching people roleplaying, and even with mentoring of players IC'ly from everything of battle to trade to whatever(I have taken Swordsmanship In the real world for example, but I didn't know everything I wanted to teach, so I spent time researching. Cept I was tad dry at that time!)
Presently I seek apprentices for Lan to teach. Are you ready to do the same, even if you are searching? Here's an example of what I did for IC and OOC use when it comes to Apprenticeship. It's a tool that Lan wrote(I wrote, the cheap sod just took credit.) It's a suggestion or at the very least a self-guide if you don't want to do this. However, like I said, it's just an example!
This is the refined end result of several different sites and hours of research and re-types. It's not easy taking on the role of a mentor in a subject. Roleplaying it is even more difficult for all the reasons in the world. I hope I didn't discourage you, but if I did, that just means you've not the confidence just yet; Which you'll get eventually from learning and understanding the material. Don't lose heart.
If you've any questions or want advice(If you've not been offended by now), then don't hesitate to send me a letter in game to the character Lancastor or drop me a tell. I'm always willing to help players if I can. Especially with RP. However if i'm never on when you are, then I think mail would be the key way to go, being as I am in a time-zone outside of The United States presently.