I'll never criticize anyone for choosing to emigrate/immigrate from/too where ever they want, Many know I left the UK for the US to work for six-12 months, and here I am a US Citizen 28 years later.
In my opinion, the single best thing about Windsor is that it's next door to Detroit and you have access to all the sporting, cultural, dinning experiences that Detroit has to offer. Honestly my view of Windsor has always been that it's a bit of a E36 M3 hole (sorry, YMMV), a place that has to be traversed to get to the beauty of the rest of Ontario. Detroit gets a bad rap, and there are some on here who go out of their way to bash it, and others like me who constantly talk it up. Both sides have good and bad points to support their view. You must remember that Detroit is a huge city by land area compared to it's population, the original built for the motor car city. Now, all the bad stuff you read about is true in some areas. But I know plenty of people who live inside Detroit, and it's a wonderful safe place to live, socialize etc. in the good areas. There are also some bad terrible areas, but on the whole, it's very safe in reality. A lot of the murder and violence, while true, is in certain areas, that most, even those who live in the city never go too.
Toronto is a beautiful city, London, Port Stanley, Niagara on the Lake (not Niagara), and especially Stratford are exceptional, but honestly Windsor leaves me cold. The bottom tip of Ontario does have a micro climate, which is why you get all the vineyards and wineries in the Western tip towards Niagara.
I do agree about how clean it is in Ontario, and Canada in general. I started a post on here a few years ago about just this subject. My feeling, and it was generally supported on here, was the big difference between rural America, and rural Canada, is that in America people have the view "It's my place, my freedom, berkeley you if I want five cars on blocks with weeds growing up around them, moldy couch on the porch with a busted coke machine. This is America and don't tell me what to do", where the prevailing sentiment in Windsor was one of pride, with most rural homes, farms, being absolutely immaculate. Now yes, before people jump up and tell me to get lost if I don't like it here, calm down. That is just one aspect of what makes living somewhere good or bad.
I hope your plan works for you, it will be interesting to see if you can find a remote gig from Toronto. I'd advise spending more time in the toe of Ontario before deciding on Windsor, as I say, the general area is nice, but I don't think Windsor itself is anything special.
Note. E36 M3ty spelling grammar and holy run on sentences Batman. But screw it, you kinda get my drift.