I acknowledge gear counts for something. However I don't think gearing contributes to my issues much, I run the class quest armor and with some Ironwork accessories and main weapon (total I-lvl as of this writing: 100).

What I dread now, even with what I feel is decent gear for ARR MSQ content, is the trials. In several trials I was the only one who got killed (Ifrit HM, Titan HM, Thornmarch) so I assumed that not only the others had more experience, but more skill also, with several people that ran the EX of it, and killed it synced.

That, right here, is a red flag, and bridging the skill gap would require me to consistently pull my weight in killing EX primals at a minimum, and synced.

As for dungeons, I can decently run a few of the non-MSQ ones at lv50 but I fear that won't affect whether I have the skill required to defeat Bismarck (or other HW MSQ trials) because my past experiences with primals led me to believe that I can't.