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Is part 2 only supposed to work on Death Marshals or should it be Guild Marshals? It seems strange to me that the model that gives the Relentless ability doesn't get to benefit from it. Since, AFAIK, there are no death marshal enforcers, henchmen or leaders and they are the only models that can take the upgrade.

I don't understand guild very well (arcanist/never borne here), and this probably doesn't answer your immediate question. But I know it's the same way with rasputina's subzero. While it can be taken by the ice golem, it's more likely taken by rasputina as the golem needs to up his pitiful defense.

In that condition, with that upgrade it only really effects the minions and not the one who takes it. It's still a fantastic upgrade and worth the 1ss.

It's all about synergy...

The Judge is a Guild Marshal in his characteristics, so he can take the upgrade (along with the Lone Marshal and Lady J)

The relentless benefits the friendly Death Marshals you hire in the crew. If it benefited the Guild Marshals you'd destroy Terror bomb threats as no one in your crew would ever take the Horror duels (assuming a crew of Lady J, Judge, Lone Marshal and Death Marshals)! That would be very powerful as lots of models in all factions cause all kinds of terror.