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Some things that stand out to me:
You're using your router's default DNS as the upstream server. Try specifying an upstream DNS in the settings instead.
Try Pihole + Unbound
Could you provide an anonymized example of how you set up the local DNS entry? E.g. Domain: sub.domain.com IP: 192.168.X.Y
Thanks for your reply. I think I managed to solve this issue and have updated my post to reflect this. Apparently I had a setting disabled in Pi-Hole which caused my DNS requests to be forwarded upstream for some reason, even though there existed a local DNS entry.