I'm lvl 27 and I checked literally every inn in the province and I cannot find this guy. I hope this isn't a bug because I created this character to do the Daedric quests because one of them was bugged on my main. Anyway I know I need to be lvl 14 to start the quest and I heard that he is in the first tavern you enter after hitting lvl 14 and that his location is fixed after that. I literally checked every inn/tavern/whatever in every city and settlement and I cannot find him. I figure it's bugged or I'm missing something. Thoughts?

PC or console? If you're on PC, press the "~" key to open up the command console and type "player.moveto A96A0" (without the quotes). This will move you to Sam's location.

If you're on 360 or PS3... keep looking lol.

he didnt show up for me until level 52...

I think he's random, so he moves between the Inn's and such. Although you'll never actually catch him travelling.

Well, there's your problem right there: you don't find him...he finds you.

On both of my playthroughs he was in Whiterun (Bannered Mare). I've never made written notes, but it seems most people find him there. And many people theorize that you'll find him in the tavern in the cell in which you spend the most time. FWIW: I probably spend the most time in the Whiterun area because of the Alchemy and Smithing convenience so my experience supports that theory.

He's drunk somewhere

Actually in my experience, he stays put in one inn. I use a 360, I'm not sure if it's different on PS3 and PC.

Anyway, the quest only ever shows up in your journal once you get close enough to Sam for him to offer you the drinking contest so that could be why it hasn't turned up. Anyway yeah, he appears once you hit level 14, maybe even at the first tavern/inn you visit after leveling. I'd just check the inns in every town/settlement you may've visited at that time, or just all of them to be thorough. He's shown up in Riften and Whiterun for me, but he showed up in Ivarstead on one of my friend's games, so I'd check every damn inn.

Mostly the places I've seen him have been Whiterun and Riften.... I *think* (I've had a LOT of toons now deleted.... most of them spent most of their time in Whiterun and Riften....) ONE of them ran into him in Riverwood.... ONE of them ran into him in Solitude.... ONE of them ran into him in Rorikstead. And no, I don't remember what any of them were doing at the time or why they were where they were.... They're all long gone to the bit-bucket in the nether.

How unreliable Mr. Guevenne is. Oh well, I'll just keep searching then.

Yeah, as gross as it is, I'd just check every inn and tavern again. Here's a list of them so it's maybe a bit easier:

http://www.uesp.net/wiki/Skyrim:Inns

Good luck.

FWIW, I met him in Ivarstead the first time I visited that town.

He has always been in the Bannered Mare in Whiterun for me.

Another vote for Bannered Mare.

What I have to know is whether this is a bug or if there is some prerequisite that I missed or something else. Do you think I have to finish the MQ for him to show up?

It's frustrating because I had to create this character to do the Daedric quests because my main triggered the Discerning the Transmundane bug and this is the last Daedric quest I have to do for this character to get the achievement.

AFAIK the only requirement is that you have to be at least level 14. He can spawn at a number of places, so just keep on looking.

Didn't finish the main quest (not a single one of those bigger quest lines actually), and met him pretty early (between levels 14 and 16) in the Bannered Mare at Whiterun.

He always appears in the inn closest to the place where you hit level 14. Since you won't remember what you were doing at that point anymore, you need to either use the console to move to his position or check out all of the inns; including the obscure ones in the wilderness.