Older content feels awful because of both the fact that its been nerfed to hell and we've got new abilities we didn't have back then as well as potency increases. Pre Shadowbringers content is not scaled for your 700 potency drill, for example or the crazy potency Picto palette spells.

It's probably always going to be that way because most roulette runners just want a fast turn off your brain 10 minute mindless run so the devs have no reason to touch it. Just look at the Crystal Tower ilvl exploit as evidence of that before it was changed.