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I think you can expect 14-16 weeks if you do all the raid bosses that drop legendary items every week. SoO drops them as well as the t13 bosses for the Sigils of Power and Wisdom.Speaking of legendary quest, as a returning player is it even worth to do that quest line? I know I need tokens from the 1st tier raids for the questline and I was wondering how are the drop rates on them? Will it take forever or I can get them in a few weeks?
The only 100%, non-RNG cockblock is step 3 where you have to get 3k valor before you can progress. This obviously takes a minimum of 3 weeks.
Edit: If you start this week you will almost certainly be able to enjoy it for a couple months before WoD hits.