Is bounty hunting a radiant quest?? or is there a set amount done base on the hold you are at?? In other words will every hold have a bounty on a randomly generated bandit or Dragon??

As far as I know it's radiant, in that there will be an infinite amount of them. However, there are only so many dungeons in one hold. It's possbile that getting a bounty will immediately reset a clearned instance of course, but I'm not entirely sure of that.

Anyway, yes, I do think you can keep doing them for as long as you want.

I'm pretty sure you're correct - this was the case for me and the mammoth tusk mine near whiterun, iirc

Alright I like that I know its not a huge feature but it does seem fun just playing a bounty hunter every now and then lol ty

I've definitely seen a quest generated that sent me to a dungeon I had very recently cleared - kill Bandit Boss X - and the dungeon was repopulated. The exterior - small bandit camp outside the dungeon entrance - had not been repopulated.

agreed - it just doesn't pay very well =(