I could also "purchase" the free PS5 version of all DLC I have bought expect from Southeastern High Speed as well. Can't comment on the download error as I don't have a PS5 yet. Edit: I could add it just now, maybe it just needed a few more minutes.
I had the same on these plus baby bullet. Try them again and again and they will pull through. I have all DLC now in the queue apart from GWE.
Hi folks. We posted a thread here about how the rollout process would happen. There is an update due later today which will enable the remastered preserved routes (this is for non-US players). In the meantime, please do not repurchase any add-ons you already own. I'll update this thread when it's live. If you're still experiencing issues after that, please let me know and I'll pass it on.