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Use a less-populated world for best chances. You may get lucky and wind up as each other’s target. This is best, then you just teleport to the target, and you don’t get a penalty after killing them.

2) Transfer relatively small amounts each time (~1 mil) in case you get jumped and lose your items.

3) Do it on non-member’s world, so the other people in the cave will be less powerful (no ancient magic, whips, etc).

4) Bring lots of food and good armor / weps on your lvl96 in case you get attacked while waiting out your penalty.

5) Bring good food on your lvl 54 (wear full rune too) in case you get attacked trying to find the lvl96.

6) Do your fighting away from the cave wall, so that other people don’t see you.

Party room won’t work. Other people are always there, and they’ll get most of the money.

Staking is limited to same amount as trading, and the limit is 30k (assuming both have like 200 quest pts).

And as you say, drop trading doesn’t work.

So that leaves Bounty Hunter. Your best bet for transferring it.