Since I live in Winnipeg. Here are the some local information
The highway sign on Homer's second trip is incorrect. Highway #9 (To Gimli) does not intersect Highway 1 (Trans-Canada Highway). You will have to take Highway 101 (The Perimeter Highway - Which circles Winnipeg). In the case Winnipeg would be South, and Gimli would be North. I would give them credit that Highway 9 does lead to Gimli.
The three tall buildings in the background at the "Winnipeg Pharmacy" are a good resemblance of Portage and Main (One of Canada's Famous intersections)
The last time I check, Border Guards in Canada don't carry weapons.
Homer Simpson was made an honorably citizen of the City of Winnipeg in June, 2003
http://www.cbc.ca/artsCanada/stories/homer300503
Homer Simpson (May 30/03)
WINNIPEG - The patriarch of the animated Simpson's family will be made an honourary citizen of Winnipeg Friday.
City hall will honour the beer-guzzling, doughnut-loving Homer Simpson, who was named after Homer Groening - the father of The Simpsons creator Matt Groening.
Last year, Matt Groening revealed his father was a native of Winnipeg.
But controversy has begun to swirl about Homer Groening's true origins.
According to the Winnipeg Sun, some have questioned his Winnipeg roots, saying that Homer Groening is actually from the tiny village of Main Centre, Sask.