I have never had this problem, but I have heard of its existence. I haven't played Skyrim in two years and since the remastered version came out I decided to play it again. I thought to myself, well, surely they fixed a ton of real bad bugs they may have learned about over the last five years. I am sure they have, but I guess this one has not been fixed/addressed. I have always been able to work around crashes and other bugs and I have tried everything for this bug, but I am STUCK and I have completed around 80% of the game and I will quit before starting a new game/character mostly because there is no guarantee this will not happen again.
So the problem is as you would expect. I defeat Whiterun's forces and am supposed to report back to Jarl Ulfric. I am unable to. No dialogue option whatsoever. I have tried every fix I could possibly find which consist of:
1. SetStage console commands (maybe I haven't found the right one?)
2. Stop/Start questline console commands
3. Enabling/Disabling Ulfric
4. Going back to Whiterun, talking with random NPC's and then trying dialogue again with Ulfric
5. Continuing on to the next Stormcloak camp to bypass Ulfric interaction
6. Leaving for four days and trying again (I read somewhere the AI may reset every four days)
7. Hitting Ulfric with sword, paying fine and trying dialogue again
I noticed upon returning to Whiterun the Jarl I defeated is back on the throne and yet he is surrounded by Stormcloak soldiers......it's like the quest only halfway completed. I think therein lies the problem. If I could get his ass off the throne and gone Ulfric would talk to me. The fact that he is still there means I didn't defeat him. I was there after the battle and I HEARD HIM SAY he will gather his belongings and leave, but he never did...
I did wait until I was nearly done with everything to continue this main quest and maybe along the way I broke it somehow, but I played Oblivion the same way. I always do everything else before doing the main quest. I have done it this way before in years past and have always completed the game. I only usually have issues with crashing like in all Bethesda games, BUT I will say, the crashing in the remastered Skyrim has CEASED entirely.
If ANYONE has another possible fix I did not mention, please let me know.