Everybody, thanks a lot your for your advice, it was very helpful.
However, after a bit of further research, I am currently leaning towards multiclassing with a Monk(probably a Helwalker). Sure, the Rogue passives and defensive spells from Trickster are great and I like Sun and Moon/Tuotilo's Palm combo, but doesn't the shield need Monk fists to be viable as a weapon? Also, Monk has access to inspirations, still a few usable full attacks, +10 int (and potenially +10 might as a Helwalker), and weaker, but still useful defensive buffs, and as Constentin mentioned, better crit synergy with Swift Flurry/Heartbeat Drumming.
This combination seems like it would greatly improve Chants, Invocations, and overall crits. On the other hand, survivability would be worse (especially as a Helwalker), and neither Chanter nor Monk seem to get a lot of accuracy bonuses to get those crits in the first place.
I couldn't find the answer to this question anywhere, but how do The Long Pain and its upgrades interact with Skald? Are they still considered melee for crit purposes?
If I went as a Chanter/Monk, which subclasses, if any, would you reccomend? +10 Might from Helwalker is very attractive, but looking at taking +50% damage, maybe FF would be a better choice. Also, with lower accuracy and therefore lower crit chance from not being a Rogue, wouldn't a Troubadour or no subclass work better in this case? Is Bellower any good?