I have both in my car for my daily travel to work and I discovered that Privateering has aged very well and I like almost every song, even the blues ones, except "Miss you blues" that still sounds as a boring nonsense to me, and that Tracker has aged for me very bad, I only can listen to "Laughs and jokes", "Basil" and then I skip every track until "mighty man", then skip until "Silver Eagle", and from there, skip songs until "Oklahoma ponnies" and "Time will end of sorrow", the rest are so boring to me that I can't stand listening to them...
As far as Tracker goes I agree with you totally on song choice. Those you listed are my favourites by a country mile.
Privateering doesn't interest me much these days. Only a few nice songs but no great ones:
Haul Away - nice little tune but no classic
Privateering - good sea shanty but annoyingly repetitive lyrics
Yon Two Crows - what seems like a minor classic at first eventually fails to deliver
Kingdom of Gold - moody but subdued number
Bluebird - underrated song in a sense but I never feel interested in listening to it much because it doesn't offer much.