rab - No, but getting closer
Boolbar - No, not exactly, but excellent guess. Winning could be considered a part of 'it'
Inkspot - No, but the portent itself has a connection
Kim - Not directly
Software - Yes
Dazed - No
Inkspot - Yes to 'occurring event' as for 'natural' - I would say more 'yes' than 'no', although the mathematics might prove otherwise [Clue#4]

..... that's close enough. The answer was 'serendipity' but as this one has dragged on for a couple of days now, it may be best to leave it that a combination of your two guesses will do nicely. [insert smiley face here] I'm pleased because I was a-rootin' an' a-tootin' for you. So whilst ...
*the audience whoops and hollers [and exhales a collective sigh of relief] and waves handkerchiefs and garters and all manner of private apparel for that vair vair clever Raak*

... I shall prepare myself for the possible questioning of some of my replies :-)

Congrats Raak, and about bl***y well time!