For those in the know, how important does OSB become for future fights with the difficulty ramping up? Doable without, but a major QOL upgrade, or is it going to be necessary to run with at least one in your A-team?
Mostly not very necessary. BSSBs do the same job better for the most part unless you have the ability to boost the elemental damage and build your team around it.
I've had Squalls since it was released without that possibility. Anything where you want to do a serious amount of damage aka Ultimate and higher you'll be hitting for between 20,000 and 40,000 and mostly the lower end WITH shout and debuffs and no haste and burst mode and only hitting 40,000 - 60,000 if theres a weakness to the element (ice for Squall) and that's still more than likely at the 40k mark depending on defense.
However, during OSB fest I pulled Clouds and Terras OSBs. While trying to get Clouds first time around I got Cid's Goggles (boosts wind damage) and clouds armour (enwind SB)...been 99,999ing the ultimate multiplayer bosses since...of course in order to enwind you've to use the other soulbreak instead of his OSB once...
Terras is a magic based one with a silly multiplier like all of the magic OSBs which requires much less shenanigans however...I have an 8* Fireship for my Krile so sheepsong, Onion Knight BSSB RW, wrath the crap out of her and happy days. I imagine multi-wrath/lifesiphon and entrust shenanigans could melt anything if you'd the orbs.
TLDR: If you have the right gear to support an OSB with the rest of your team they can be incredible. Lumped in with a balanced A-team, not so much. I dropped Squall from my A-team in favour of others with BSSB...now I don't know which to run, Cloud or Terra and let the boss itself decide for me...