On this character I'm not getting random encounters, well I've gotten a few like a few thugs that were hired by a Forsworn I pick-pocketed... but ones like the letter from Calcelmo never happened even though I spent a small fortune buying Dwarven items from stores all around Skyrim and even the Boethiah cultist that's supposed to attack you has yet to show even though I'm like double the level requirement for that encounter now.

So, is there a way to jump-start these encounters? I managed to get the courier for old Calcelmo to spawn by resetting the quest but the same doesn't seem to be true for the cultist.

Actually, I never got the random encounter after completing the quest for Sanguine either... Is my game borked, why aren't they showing up?

I'm not one to bump but this thread is so far off the front page it isn't even funny.

Well, im not very good at console commands, but you could try to spawn said boethiah cultist (assuming he has a NPC reference thing) and he might do his thing?I've no idea if theres a "spawn" command, but at least you can teleport the cultist to you. If he exists, hah.

I had tried to but when he spawned he didn't have the book on him and he didn't update the quest, I've since started a new character and he attacked me in the first few hours of play.

For future reference, once you hit level 30, you can activate the quest by going to the shrine by yourself or by reading the book in Septimus' outpost up north.

You're going to think I'm crazy but I already knew that, for my playstyle I kinda wanted to be attacked and find out that way. >.<

For that Boethian cultist: My current character hasn't encountered that one as well. And I have somewhat of an explanation for him being missing, from a previous character of mine.

That one had just turned level 30 when she went into that room with Skjor and Aela and they turned her into a canine. She left the cave in horror and went running through the farms near Whiterun, when a Boethian cultist approached her... and actually killed her because I'm really inept at melee and hadn't been bothered to put any points into health. I had to reload. The cultist then never spawned for this character again.

So, my guess is that if you run into a unique random encounter like the cultist, and have to reload, then the game will still think that you've had that encounter now and won't ever repeat it for this character.

Maybe my current character reloaded because she was killed by a sabrecat just when the cultist approached her. Maybe she just snuck successfully past the weirdo. Maybe your character did something of the same kind.