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Yes, it does hurt when they update and adds the extra interest to the debt. Definitely look around to see if others had PFD success with that creditor. I don't believe in the word "impossible" but I know that some are. IMO, if they reject your PFD attempts month after month, then PIF and then start GWing.
The delinquency is just one delinquency. Monthly "updates" are simply continuing to report that delinquency as the current delinquency status of the account.
It does not add an additionaly delinquency. If the account was 90 days late and remains unpaid, they could have legitimately reported higher levels of delinquency, so continued reporting of a 90 late is probably to your advantage rather than disadvantage.
I presume the account is now closed? If so, it wont be updated to paid as agreed, which is a status for an open account in good standing.
It will simply be updated to paid, $0 balance. If you reach a settlement for less than the full amount, it will still be reported with a curent status of paid, but they can additionally report a special comment of paid for less than the full amount, which is a negative comment in your CR.
If they wont do a PFD, I would at least attempt to negotiate their promise not to report that additional special comment of paid for less.