With that many teams, maybe the CFL would have become sort-of a minor league for the NFL in that they would be getting more players from that league than they were before with 20 teams instead of what they have today. The Cameron Wakes and Philip Hunts would be a little more common.
Also, Dude, I will bring up an idea that you posed earlier on this page. I think that this "Sports What-ifs" thread should be stickied at the top like the pop culture thread. Either propose "what ifs" or have links to timelines. And, I think that all the pages of this thread should be deleted except for the first page and the last 5 pages.
I would propose starting a new one entirely, if we're deleting pages, since a pinned topic would bring more fresh eyes onto these what ifs, and if they are proposed again we could have new, more exciting discussions with more members. I feel sports what ifs could become bigger, especially with people like me who are getting bored/feeling a little dirty talking about all those war alt hists.
As for the CFL: I'm not really sure if the league would be okay functioning as a minor league. Since the 80s, the league has had a bit of an inferiority complex when it comes to the NFL, a lot of it being the NFL having a much larger advantage when it comes to television exposure. I could see the NFL proposing such a plan, and the CFL promptly rejecting it. This could result in a legal battle that ends with the CFL agreeing perhaps to limit their American franchises to the six locations already mentioned.
I think the CFL would still want 20 franchises, though, since it's a nice, even number and I feel the league could support it, American franchises or not. In this case, I see Quebec City, London, and Windsor recieving new franchises, and the Alouettes being started up again in Montreal relatively quickly. These are large cities, and I feel that they wouldn't significantly cut into other fanbases/media markets enough to cause a stir among the existing CFL teams.
So now we have six American and eleven Canadian franchises. This is where it gets a bit trickier. The next two cities that seem most interested in a franchise are Moncton and Saskatoon, but, in both cases this would be causing problems for what are in this timeline established teams. Moncton and Halifax are the two largest cities in Atlantic Canada, and both seem to be insistent that they, and only they, be the ones to recieve the long-discussed Schooners franchise. If Halifax has recieved it already (and at the time they were more likely to) then Moncton might be a dead letter. The problem with Saskatoon is that it's basically slicing the already small Saskatchewan Roughriders market in half. Saskatoon is also twice as large as Regina, where the Roughriders are located, so it might even be a larger loss than simply half.
At this point, the best choices for expansion might be again in the United States. Anchorage, Alaska, and Fargo, North Dakota are good, out of the way places, and I doubt the NFL would care to see those markets go when it's base is obviously the continental United States and usually not right on the border. This brings us up to 19. For a 20th team, perhaps a second one in the Toronto area? Waterloo could probably support a team, unless they decide to double up in Atlantic Canada.
So by 2000 the CFL looks like this:
Eastern Conference:
Northern Division:
Halifax Schooners
Montreal Alouettes
Ottawa Renegades (*)
Quebec City, Quebec (Rebelles?)
Toronto Argonauts
Southern Division:
Columbus, Ohio (Tigers?)
Hamilton Tiger-Cats
Hartford, Connecticut (Colonials?)
Rochester, New York (???)
Windsor, Ontario (????)
Western Conference:
Eastern Division:
Edmonton Eskimos'
Fargo, North Dakota (Liberty?)
Milwaukee, Wisconsin (Maurauders?)
Winnipeg Blue Bombers
Saskatchewan Roughriders
Western Division:
Anchorage, Alaska (???)
BC Lions
Boise, Idaho (???)
Calgary Stampeders
Portland, Oregon (Breakers?)
The Ottawa Rough Riders are probably still going to fold, but if "CFL USA" is more successful there will be more money to start the franchise up sooner. I gave them the name of the franchise that did replace the Ottawa Rough Riders in this world.
Names in parenthesis are my guesses at team names, mostly based on previous team that existed at that location.