Don't know about the smoking outfit, or that Cockburn's.
Try: Fonseca Bin 27, Six Grapes, almost anything by Sandeman (the cheap stuff is fine) or Jonsey. All of those bottles can be found in the $10 - $25 range, aren't too sweet, and should give you a good start to port. I find it a really nice complement to a cigar.
Avoid Christian Brothers.
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