I think it’s cool that you want to move from a condo to a house at this stage of life, usually as people get older it’s the opposite, they don’t want the house that needs constant maintenance. I agree with the selection of towns you mentioned, except for Oshawa and Barrie. Personally, I know people living both cities and they are always complaining about a rising crime rate and home break ins.
I'm surprised you say that, all people of my age that I know want a house (or ideally want a house). I think for retirement condos are great so not cancelling out that later in life. As for crime every city/town has it, the correlation is - the more expensive the town the less crime but for expensive you need money :) plus a lot of times pricier cities are more relaxed and there is far less to do.
