I start to get the feeling that the game by its design is assuming roulettes are used during leveling along with MSQ. So I wondered if side quests can be an alternative.1. If you aren't sharing exp between classes, msq should be enough to get you through stormblood. Though if not, roulettes are your best bet. Also if exp is an issue now, you definitely won't get through shadowbringers without a bit of grinding (which is generally standard).
It is not mandatory to level or even unlock the chocobo for combat purposes. It's just handy to do so. I do recommend healing over damage though but its 100% up to you.
As for my chocobo, I have it on Free stance, and the little guy does try to heal me whenever my HP is not full.
It's a personal thing. I'm used to run dungeons at level cap, when I switch to my "end game" mode from "quest/leveling" mode. In FF14, dungeons are also intertwined within the story line, rather than optional. It kind of feels weird to "relive" something that I've already done/killed, when I'm "immersed" in the current story.
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