add to the list of things that don't work to get this quest going/getting the house
1. enter/leave city several times entering at night, many times after 2am
2. pickpocketing the hjerim key from tova shatter shields body, entering hrejim, and getting the 2 journals and amulet to trigger quest
3. try talking to everyone in windhelm w/ and w/out evidence
4. doing the stormcloak side of the civil war till given the option to buy the house but the "unpleasentness" prevents that, damn stewart
this quest is horribly bugged, while looking for answers I've come across multiple PC players unable to start this quest even w/ console commands, that is bad
Doing the Imperial side has the same result as #4.
Number of times entering or leaving is irrelevant. My oldest character had never managed to trip this quest; another got it on her first time walking into Windhelm.
The 1.4 beta fixed it for me- my oldest finally got it on her next trip to Windhelm, right after installing it. I started it in the early morning, finished off the real killer by afternoon. Either time of day/night requirements have been removed removed from the quest, or the bug with days being out of sync with the time was royally messing it up (for those who didn't know, the day of the week was not changing at midnight; fast travel and carriage use threw it out of whack, along with all the NPCs' scheduling).