Bit of both. lol WWE came here more when house show business was down because Winnipeg was always a really strong revenue-per-person town (ie. tickets, merch). When house shows exploded, Winnipeg was still good but other places were better and with the US dollar and easier trans, they came to Winnipeg less.
Another big issue with Winnipeg is getting TV trucks in here and then out to the next town they want to run TV. Thats why in 2005 (I think), they did both RAW & SD here (and sold them both out which was amazing). In the 90's, when they added the In Your House PPV's, they had a Winnipeg date already so kept it for the PPV and ran Brandon, as I recall, for RAW and Brandon is awful for wrestling.
After the double shot TV in 2005, it was believed WWE would be back quickly for TV, but they werent. When the new arena opened, I remember Bob Holiday (then the local WWE promoter) saying they'd be here for TV when it opened and they werent. Just the economics and trans.
Id suspect they're coming back because their house show business is down, but Winnipeg is still strong, their TV show attendance is also down so they probably see Winnipeg as an easy sell out and a hot crowd. I sort of wonder if coming to the hometown of Kenny & Jericho factored into it lol (maybe they're aware of an AEW Canadian tour...?). It might sound silly, but WWE would absolutely bring TV to a city they dont go to often if they thought the competition might.