Registering a used boat without a complete chain of ownership from the last registered

owner of the boat. How hard is it? My buddy has a little all weld boat that he wants to put a motor on. Here is the info he has from when he bought it:

Affidavit/Court Order recognizing that man he purchased it from was the legal owner

The former owner's notarized bill of sale from when he bought it

An affidavit for boat inspection since the HID was illegible (notarized)

A notarized bill of sale from him buying the boat from the previous owner (who had an affidavit stating his ownership)

From what I've read this should be enough, he is going to try and get his own affidavit stating his ownership. The previous owner said that even with the affidavit he could not get it registered. He claims that since they don't know who originally registered the boat that they cannot. I don't understand if the HID was ineligible how they would know who registered it.

Is it a hopeless cause?