While I disagree with several points in your analysis, the conclusion reached isn't bad. WoE 1.0 and 2.0 were on diff days on the iRO Valk server for similar reasons.
Alternatively, it might be possible to leave the Ald castle with the current drops (and perhaps an improved upper limit on chests?) while giving the new droplist to the trans WoE castles.
That being said, I prefer the former solution to the latter.
[edit] Also, if the pre-trans WoE did get it's own day I feel the participant list should be expanded to include the extended classes as well.