I agree with CTHabsfan here. Saskatoon probably can punch above its weight; however, Winnipeg, owned by a fabulously wealthy man who brought the team back to Canada as a point of civic pride, knowing the financials were tricky at best, is already making noises about how difficult it is to justify financially. The NHL's going to be looking for more stability than that, and a market that absolutely has to continually punch above its weight, in good times and bad, will almost certainly not be the league's first, second, or twelfth choice.
I suspect that the barrier for entry for any city going forward, unless there's a Ralston-Purina "take the team or we fold" situation or the very specific case of Quebec City getting their team back, is a metro population of 1M+.