Hello, sorry for my delay in responding.
YubiKey advises against eliminating the PIN policy. To prevent it from asking multiple times, you would have to delete the certificate and import it again. But for this, you would have to readmit it again and wait more than 2 business days for approval.
This also wastes a lot of time but as I said, yubikey advises against it.
In an external updater package that I have, with a bat file I sign an entire folder at once and it only asks me for the PIN once, this is something that I have developed on my own to avoid having to enter the PIN several times.
Maybe advanced installer, you should do the following:
Enter a new configuration specific to signing with YubiKey keys. If the user has selected this, when the installer construction is launched, create a BAT file where it contains all the files that must be signed, this way it would only ask for the PIN once and not every time it has to sign.
It may be a solution.