So I got the radiant quest to get [censored] bag some black briar mead. In the process of me getting some (waited a few hours, was doing other stuff) the quest failed. Well, eventually I got a letter from said [censored] bag saying to come talk to him about buying land. I go to talk to him, but the only two dialogue options available are the generic ones about why hes amazing and whatnot. I can't even reaquire the radiant quest. His steward is useless also.

Anybody in the same about? Fixes? Etc?

Once you receive the letter from Jarl Siddgeir, you have already 'fulfilled' the quest for the mead. (I only discovered this when I went to him myself after getting the letter and found I no longer needed to deliver it to him). I was in the same situation as you until I realised I had a similar quest in my misc objectives. By completing the quest, the dialogue options came back.

Hope this helps you.

Yes, it seems if you have another 'fetch this' or 'retrieve this' type of quest, you need to complete that. Two of them going at once bugs things up. Quite a few people have said once they cleared those quests, things then went as they are supposed to.

Happened to me with the quest in Windhelm regarding delivering a book. Was most annoyed at what I thought was a glitch, until I discovered I had to clear my already pending delivery quest.