Have you ever postulated on the exact nature of the feudal hierarchy of the Gifts, especially concerning the possible differences between Brandon’s – and the New Gift. From the text, tenants of the lands in the Gifts paid socage to the Watch, yet this did not include military service? So is it rather a bastard form of Quit-rent to the Watch while owing fealty to the Starks of Winterfell?

I don’t think there is a difference between the two gifts. I think the tenants pay (or at least paid) rent in kind – food, horses, etc. And that food supports the Night’s Watch, who do the military service. 

And no, the tenants don’t owe fealty to Winterfell, as technically the Gifts are separate from the North. Hence why Torrhen’s sons were so pissed off about the New Gift. 

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