Showed to my DM, I think he now has it framed
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No, you cannot attach a drop to this castle and drag it across the countryside, even with a nat 20.
What if I use a pulley?
Was the pulley created by Karsus? Then yes.
Legendary item Karsus's Pulley.
When you fail the history check, and recall your teacher mentioning something about Karsus's Pulley in the year -339 DR. "Can't for the life of me remember how he managed to kill magic with the thing..."
is Karus , the blacksmith from that village over there good enough ?
No, He has to be sus.
Thus begins the Mortal Engines campaign