Those franchises moved at a time when the NHL was making "a lot" more money than they are now. The US dollar was strong against the Canadian dollar and the league thought it had a chance to grow in the southern US. By comparison the smaller Canadian markets couldn't compete with the US cities for dollars. Those moves never would have happened today.
The mere fact that they put the Stanley Cup on the “Outdoor Life” network instead of ESPN2
That did that because ESPN didn't want them any more. Their financial offer was so far undercut and the league had such bloated salaries and expenses that it needed more money if it was to survive. Granted, it was their fault that they didn't realize the golden goose was dead.
I agree with you that the marketing and strategic planning of the NHL is horrible and always has been.