I don't know how I ended up asking about Pusser's over here on this thread, but I've spent a week (a little more) with it, poured about 1/3 of the bottle and am still in the process of acquiring a taste for it. However it is getting easier to drink and helps me appreciate the sweetness of my otherwise less-sweet rums -- the unadulterated ones. It has also had the effect of bumping the sweetest rum (Diplomatico R.E.) out of my rotation because it now comes across as much too sweet.
As for cigars, the Pusser's not only pairs well with a strong cigar, it requires a strong cigar. If you try to pair it with a mild cigar the rum completely overwhelms the cigar's flavors and you taste nothing of the cigar at all.