My question is, if he pays her $2,000 is he hoping that she just goes away?
You're not paying $2,000 to go away, you're paying $2,000 in exchange for the right to sue. If he pays without going through a lawyer she could still sue him and be up an extra $2,000.
Essentially him paying her $2,000 and ignoring her has the same outcome, she can still sue him (unless he goes through a lawyer and has a form drafted outlining the agreement, I doubt that he'd put one together himself that would prevent this). The end effect is identical.
For the love of all that is good and holy get him to call a copyright lawyer. If he's worried about having to travel to Calgary, call the local guys first, see if someone there can do it (you'd be surprised at the expertise in your own backyard) if not then call Calgary before travelling. With today's technology a consultation can be done over the phone with required documents scanned/emailed, or even skype. The location of the closest lawyer is not the issue it was even 15 years ago.
DO NOT SEND ANYTHING WITHOUT TALKING TO A LAYWER
I can't stress the bolded part enough.
I see your point on a lawyer could end up costing $2,000 but remember just sending $2k on a wish and a prayer isn't doing to make a tinker darn of a difference.
** Also of note, I'm not saying one side is right or not, just talking about process I don't know anything on the actual legal issues at hand.
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