The most honest answer you will get is the time-frame is unknown.
LW are fully focused on the content market. I would wager a guess that we won't hear anything about other big additional features until that is implemented.
My feedback... for what it's worth. My player's didn't use Obsidian Portal even when I did populate it for my players. And for that reason the tool choice I have made is a selfish one. RW smashes the competition for functionality with the exception of web access.
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D&D 5e Community Pack - Contributor
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D&D 5e Community Pack - Install Instructions / D&D 5e Community Pack - Log Fault / D&D 5e Community Pack - Editor Knowledge Base
Obsidian
Obsidian TTRPG Tutorials
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