Mindestens

With all the bugs currently still in the game it's a very low priority thing (maybe something worth considering with expansion/sequel), but I find it a little bit odd that player doesn't get belongings of prisoners. It's something I noticed with Nyrid, but I didn't pay much attention as he didn't have any unique loot. Then I captured Gramrfel the Wayfarer, and since I killed him before a couple of times already I knew very well he drops Dead Man Stands boots. It was a real bummer when I learned that by sparing his life I didn't get them - especially given the fact that so far Dyrwood seems to have shortage of shoemakers as I found just three pairs of boots in my travels. Maybe the big bad isn't after what he seems to be but really wants all the shoes in Eora. Now that would be some twist. Maybe prisoners are so keen to escape because no one disarmed them before throwing them into cells. If they were, I could certainly use some of their things. Both times I checked corpses if I the loot was there anyway, my inventory and combat log if it was added there somehow, I also searched treasury and stash. My jailer and the prisoners themselves also had nothing to tell me regarding things I should confiscated. Also, would be cool if prisoners wore some rags instead of their usual attire, but now I'm just daydreaming.

It may also have something to do with queueing orders - the only character I ever used it for is Sagani in my latest playthrough for Marked Prey followed by Wounding Shot - every couple of fights I notice MP becomes unusable until I load earlier save file. It never happened before and in none of my earlier attempts at the game I tried using queue in PoE. I think the issue could be caused if targeted mobs got killed before whole queue played out or if mob was killed before it even started.

Can only speak about my own little experience, but the one time when I actually played for a while and got reasonably far, over 30 hours (last save file said I was playing 36h) after the first guy showed up before I had barracks built, nor he nor the others who came after showed up again. One of the main reasons why I intend to try to min/max stronghold with how it's systems currently work once the game will be patched and playable.