I really wonder why anyone would stick it out in Milton in their retirement. The only thing I can think of really is strong connection to friends or proximity to grandchildren, but with the price of real estate having gone to the insano level.. if I was sitting on a 1.5m house and could downsize easily up in Napanee to something that is half that, that just makes good sense to me. Good luck.
As for us still working, young kids, I love Milton. Full of people in our similar positions, lots of job prospects (admittedly less actually in Milton) but it is a good commute to a lot of areas. Somehow needs to buy some train track to make a 30 minute trip by train to Union and our houses would be doubling yet again