That's totally awesome! Just out of the gate, the minstrel is really flexible; he can already play: clarinet, cowbell, flute, harp, horn and lute.
So, you really don't need to even bother leveling him up if you would rather work on other characters. At level 10 you get drum, and at level 15 you get theorbo, but we don't usually have a problem covering both those instruments. You could just buy the six instruments you can already play, and be done with it.
As far as transport for Hobbedoc -- you might consider this: set your milestone for the Shire, and then get Krohkur to invite him to the Northern Lights kin for the time being (their kinhouse is where we practice in Bree)-- that way you can teleport between Shire and Bree, which is prolly the max extent of where we will play for the forseeable future.
I didn't quite realize that you could run multiple instances of LOTRO on the same box, so I tested it and it seems to work for me as well.
One issue is screen real estate. I happen to have a dual monitor setup, but even if you don't, you can run LOTRO client windowed, and resize the windows so that both fit on one screen. Works pretty well on wide screen monitors (at least, well enough for band concerts).
Second possible issue is stability of the clients. I tried it just now -- first time both clients just abruptly crashed .. not sure what I did ... but I tried it again, and they've been stable for half an hour of further testing, so not even sure if the first crash was related to the two clients on same box issue.
Anyway, as Hobbs says, it might just be a question of what your particular hardware can handle. According to this thread, running multiple clients on a box should in theory work.
And, being able to have a couple characters per band member would really help. I could even run a couple characters on each of my computers -- that would be four band members from just my little old self!
So, Dend, if you are reading this, I think we might have a way to get that 20 to 40 piece band you were thinking of!
So, hope to get out a post about next concert later tonight -- probably Silth and I will organize this next one, and I'm want to run some ideas past him first.