This particular situation is extremely questionable.
A translator that's licensed to rebroadcast an FM station can carry HD2/3/4 audio because the FCC ruled early on that the translator can carry any part of the originating signal.
A translator that's licensed to rebroadcast an AM station can only carry the one audio signal coming from the AM, because that's all there is. (If and when AM HD2 becomes technically possible, that's a new question the FCC has yet to answer.)
W255DA is licensed to rebroadcast AM station WCCM. But it's not carrying WCCM's audio. Instead, the audio it carries comes from the HD2 of another translator, W275BH, which is in turn a translator of WNNW 800.
This opens up two new questions: can an FM translator of an AM station (which has only one audio stream) originate separate programming on HD2/3/4? And can those new program streams then be relayed by an analog translator, effectively creating a new station?
W275BH has been in HD for years and the FCC appears to have tacitly accepted its subchannels, in part because they originally carried sister AM AM stations and weren't originating new formats.
But the 98.9 situation is murkier. It's in the definition of the translator service that a translator can't originate its own programming and must be relaying something originating from a full power station (even if it's an HD sub)
W255DA fails that test. At best, when W275BH is properly on the air with its HD subs (which it often is not), it's rebroadcasting programming that originates on another translator. At worst, it's effectively originating its own programming.
That's not unique - Saga has a cluster near me with three translators allegedly fed from HD subs that have been off the air for years. But at least when those are operating properly, they're clearly legal. I'm not sure you can make that same case for W255DA.