At least in 1998 they made the final table. I would be happy if they finished last in the final table everytime. That's 10 extra games. Games on tv, people talking about teams like USA and Mexico coming to Canada etc...
These days they're not even close and as you said, people just laugh and go for a bigger team.
I don't think the talent now is that bad. Put a lineup like this together.
(left to right)
Gerba-Friend
De Rosario-De Guzman-De Jong-Hutchinson
Klukowski-Serioux-McKenna-Stalteri
Wagenaar
I think that's a decent team for CONCACAF that a good coach could tactically mold into something