After doing all my testing with the random portriats mod on I've belately found out that there is a clash between the two mods. The order shown in the mod screen is important. If you have my mod in position 0 and randomportraits in position 1, some code is overwritten and there are no quests in the guild at game start. To get it to work, put randomportraits in position 0 and my mod in position 1.
Believe it or not, the obvious fixes don't work so for now please put the mods in the right order.