I was afraid of this. Winnipeg is by far the tiniest market still in the NHL. They're alright when the economy's good but when it hits the proverbial fan, it's an open question whether they can sustain. This is what killed the original Jets when the exchange rate went sour.
At a certain point you have to look at their situation dispassionately. Yes, getting the Jets back was a victory for Canada in a way, but the bottom line doesn't change. At a certain point, ownership is going to look at any one of the about 6 unserved US markets that are way larger, and say to themselves "I' definitely be making more money if I just moved to Salt Lake/Houston/Portland/KC/Atlanta/Milwaukee."
Anyone of those markets could enrich and owner more easily and more consistently than Winnipeg, and that's the sad truth.
And yet Winnipeg is a far better option financially than a overstuffed Milwaukee market you proposed elsewhere. Only 1.5 million people in Milwaukee (with 3 teams including the Packers) with a relatively small corporate base....and as we have seen time and time again the majority of ticket holders come from within an hours drive of the arena.
Salt Lake doesn't have an arena suitable for hockey and the population is the same as Calgary/Edmonton. Given the NBA occurs at the same time, it almost a certainty revenues would not be any higher than the current Winnipeg Jets. Anyways, it's more likely they will push for a MLB team as has been reported here - far too small for 3 teams. Baseball is more likely to succeed given the season happens outside the NBA schedule so less direct competition.
Atlanta's revenue doubled from 2011 to 2012 when they moved to Winnipeg. No reason to believe a future Atlanta team would become a high revenue team based on hope.
KC is smaller than Winnipeg and Edmonton put together and can barely handle two top-4 pro leagues as it is. Their baseball team typically draws some of the lowest crowds in baseball and they are usually bottom-3 or 4 in revenue. An NHL team there would further stress their situation and given the size of the community, it would likely be a lower revenue team. They would not be filling some strategic location as part of the overall footprint in the US either.
Portland is a decent sized city but not all that big and the population is no longer growing and since a hypothetical team would be competing for corporate and discretionary dollars against an NBA team playing at the exact same time, it's unlikely the revenue increase would be substantial, if it exists at all.
Houston could be an option but as has been publicly reported he was not willing the pay the going rate...and that was a few years ago, and the price has only increased dramatically. Right now, that city looks like the likely landing spot for Arizona if their arena deal falls through.