I've completed my testing and I did two tests. First, I transferred a reseller owned account without the reseller existing on the new machine yet. That account did obtain a dedicated IP successfully on transfer.
On the second test, I transferred the reseller account over first and then transferred the reseller owned account with the dedicated IP. Both tests were performed as root user.
On the second test, the reseller owned account failed to obtain an IP and did have the error you indicated:
You need the 'add-pkg-ip' priv to be able to create an account with a
dedicated ip address.Forced Dns is enabled.
We will be opening a report on this behavior now that I've reproduced it. In the meantime, the only way to successfully transfer the account is to do one of two things:
Transfer an account over before the reseller is transferred over to obtain a dedicated IP properly.
Provide the reseller temporarily with that privilege "Allow Creation of Packages with a Dedicated IP" in Reseller Center > Edit reseller privileges & nameservers area.