I am currently doing this on Test Server.
I started 54 Toons and levelled them to 50.
Raided Fear, Hate, Sky, Naggy, Vox, Phinny, Ring of Fear This is basically the Conqueror achievement.
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The Main Rule was you can only wear what you loot.
The only real annoying thing was all the ornate/intricate type armor that dropped and its so OP for the era - but Im also not getting epic 1 on any of these toons so a little OP is ok.
Ive now moved up to doing Kunark.
Killed Gore/Trak/Sev/faydedar/King Queen Prince in Chardok, VS, DS and then farm Veeshan Peak.
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It just takes a bit of discipline to hold yourself to the right era but there are plenty of things to do.
It has taken me about 6 months to go through these 2 expansions and soon ill move onto Velious, and i expect ill be 6 months in Velious before moving on.
I recommend the exercise to everyone. The only time it gets frustrating is when trying to move 54 toons through some old zones with older meshes and stupid door mechanics like in Veeshan's peak.