When Beth told me she was pregnant is when the quest "Bearer of Good News" starts. Gabriel is in the court yard to left side of the temple entrance. I went straight to him and gave the good news only to get knocked out.
There was no quest problems.
With the kidnapping of the MC it happened when leaving Gwyneth's house. I went to see her for whatever reason. Maybe for sex. Anyway after walking out of her house, bang, right up on the back of the head and you go out like a light switch turned off. Finally coming too in the hideout. It was easy to defeat all the bandits and make it back to the village in time for the election which results in the fight with mayors son. Defeated by you resulted in you being the new mayor. No problem with the quest.
Even though I had no problem of any kind during the quest of either one, I suppose that it may be possible to screw them up some way. I do not understand way anyone would go looking for Gabriel in the tavern. He gave up drinking a long time ago when he decided to join you on his first mission with you. After the orc's were defeated he told you in the court yard about training with him. So when i got the quest "Bearer of Good News" I just went straight to the court yard where I new he would be.
I suppose if someone went looking for him at night things may be different. Seeing that the kidnapping of the MC was at night. I do not think it makes any difference what building you come out of in order for MC to get knocked out and kidnapped because it has to happen at night.
For myself, I try not to do anything at night because ass old as I am I don't see things that good at night.
One last thing about the two quest. Once I had told Gabriel the good news, got knocked out, finally coming too the next day with the swamp elf doing something to me and once finished I went to other parts of the map to work on different quest. So it was several days that passed before I visited Gwyneth at night and ended up kidnapped.
Just my thoughts being expressed. I have played the game over and over mainly whenever there is an update because I forget a lot of what my game plan was. As for quest goes, I have never had a problem with a single one. I have encountered issues with other things but not with quests.