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IMB I don't require training every circle, only at the 'milestone' circles- initiate, journeyman, etc. (mostly for campaign pacing reasons-- I don't want the players to get stuck in the lower circles for a long time because there's not enough downtime. But also because I also like to keep adept's numbers down IMB, so there aren't always trainers to be found, even if there were time).

I only did one initiate advancement during play for storyline reasons. He's the son of a minor lord, so his initiation was part of a spring festival. He's an archer, so his master came out and gave a spiel about the nature of the discipline, about sorting targets from arrows, etc, and that the bow was a metaphor for their outlook on life, then the player had to make some cool shot that required actually picking the correct target (I think I might have stolen this whole scene from one of the books but I honestly can't remember, lol. My players are all brand new to ED, so I was trying to give them some hints as to how to conceptualize their own Disciplines, and it seemed to have worked fairly well).

The party is fast approaching 5th circle, and I really want to do something appropriate for their advancement to really drive home the idea that they have arrived at a significant milestones (they are now recognized as 'professional' by their peers, for lack of a better term).

Anyway, I'm drawing a big fat blank for what to do with these guys, so any ideas would be appreciated...

The crew:
Archer
Purifier
Weaponsmith
Windmaster
Wizard

In my campaigns 5th circle is the circle that allows to initiate others into the disipline, thus most trial would involve around teaching others, finding candidates.

To the archer i would give the task to shoot arrow over several thousand feet mountain.

Look for cube of metatron via google, print the picture, and make wizzard to find all cubic shapes hidden there.

I can paraprhase what happens when my PC come o their masters for advancement ( i RP every circle)

pc- I want to talk about advancement, master
m- and?
pc- i think i'm ready for the task to prove i am worthy.
m-good for you, how would you make me think you're worthy for the trial?
pc- well, i killed two Espagra's
m- and what did it teach you
pc- well how to kill them
m- and what did it teach you about your discipline, and yourself
pc- hmm i started it wrong..
m- yes
pc- Master my name is Kornak and i wanted to ask you question about our discipline, what is a reason for wars?
m- and what is war?
pc- well to me war is something i want to prevent, it would ruin my village, and other viliges,
m-and what do you do to prevent it?
pc- i went to neighbour viliage that we think stole our cows and i challenged their best fighter to settle the mattero of cows,
m- did you win?
pc- no i didnt, but there was a traveling group there and warrior from that group initiated me, after he saved me from dieing in a duel, they were there to kill horror that was killing their cows, they killed it, but not before all cattle was dead
m- so you brought back an adept to you villiage instead of the cattle?
pc- no i came empty handed
m-...yourself
pc- um, hmm yes!
m- so what was the reason for your conflict back then
pc- their stole our cows
m- why!!
pc- they were afraid they will starve
m- fear among many causes wars- thus fear we conquer as warriors
pc- dont we conquer enemies?
m- you know what, go spend the night alone in the cementary outside of town, the one thats not used, tomorrow we will talk more.

(it's not precisely what happens, but its possible scenario, cementary is ofc haunted , there is no enemy there to defeat, only ones fear- but this is more or less how i roll with my group- pr'ing advancement is a big thing for me)

lol nice convo. My masters tend to go all Socratic on my players as well.

I like the idea their advancement to journeyman involving finding or teaching candidates, I'll probably do some of that.
I also like the idea of having the wizard solve some sort of RL brain twister, I'll have to think on that more.

Thanks for the suggestions.