Yes, this ability does synergize with Sail the Azurite Sea or other effects that allow inking a card. But, it does not work with the effect like Measure Me Again from Tipo Growing Son that allows a player to put a card from your hand into your inkwell. Inking a card is a verb and is specifically different from putting a card into your inkwell
Ive organized it by a Pokemon and then by a set from oldest to newest and Japanese cards always go first as they have been released first in most cases
To start the combo, you will need to have Doubling Season on the battlefield along with Ichormoon Gauntlet as well and have enough mana to cast Jace, Cunning Castaway
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You may want to consider Reliquary Tower if you build something similar, you'll always have a full hand or more
Dragon Doomcaliber Knight Cyber-Stein Card Crush Virus Dark Magician Blue-Eyes White Dragon Tyler, the Great Warrior Were only looking at the Yu-Gi-Oh