I have seen many amazing cities in my time and many great downtown areas ... and not once have thought Regina should be a model for Winnipeg's downtown.
Winnipeg's downtown does have many great attributes, including some 30,000 residents, an amazing park area (the Forks), impressive throughfairs such as Broadway and Portage and some very urban areas. Add in some great public ammenities such as the MTS Centre, Canwest Park, WAG, the Concert Hall, the Burton Cummings Theatre, the MTC and the Pantages Theatre and a growing downtown University. Winnipeg also has some impressive corporate head offices, which draws thousands of middle and upper middle income workers into the area.
Of course there is room for improvement, but overall I would say for a city of its size our downtown pretty good. The fact that Winnipeg's downtown is spread over such a large area doesn't help create the density many of us would like, but we have to deal with the cards we are dealt. Winnipeg was really meant to be a much larger city ... Chicago of the North, which impacts it still today.
While a much smaller city like Regina can't offer the same level of downtown ammenities as Winnipeg, it still has a respectible downtown. With that said I don't remember the last time I saw 16,000 people floading downtown Regina to see a concert or event, yet on a weekly basis.