@Wise
Maybe my experiences can help.
I grew up in Etobicoke and eventually after living in public housing for years, me and the fam bought a house (bungalow) off Weston and 401 because we wanted to stay in the West but didn't want to leave the city.
After 2 years (and $70,000 in profit) we had to sell because (a) we didn't have the greatest down payment and the mortgage was killing us and (b) we got rocked by the flooding in 2013. We got a payout from insurance for the sewer back up, my dad renovated the place and we had to get out of dodge
Aug 2014, I ended up buying a house in Milton (brand new, 2 story detached, exterior brick, 401 and James Snow, literally 1-2 min off the highway, 2000 square feet etc etc) for less $50,000 less than my shytty bungalow in Weston
Now, I don't live there (Im in Ottawa) so my family is holding it down but I have other relatives who have moved to Milton, in fact we've collectively set Milton as our new base of operations.
Heres my take on Milton
Its affordable if you have your heart set on the West. Brampton is a shyt hole, Sauga is priced out, and Georgetown/Halton Hills/Acton is a bit too white for me and too far off the 401. Im a west end kid so I could NEVER move to Durham. And York Region is priced the fukk out too. Im not dropping 600,000 for a town house.
You can get a nice brand new home at a decent price. I would actually recommend buying an older house in "old Milton" and reno it yourself because these Mattamee homes are all shyt, (poor quality). Me, I don't have a single handyman skill in me, so I had to go with the new built (especially because payments are flexible in terms of down payments and you'll see a jump in value between signing those initial papers and the closing date).
The values of the home are doing really well too. Ive owned my house for 14 months and comparable homes in the area are already selling for $60,000 more than what I spent just last year. The taxes in Milton are not that bad either.
The only thing is, you gotta see it as a long term project because the citys paying catch up for the services and infrastructure. I mean, groceries, pharmacy, banks etc are all there, but the commercial is not matching the residential yet. But that could be a good thing because by the time it does you could be sitting pretty in terms of your home value.
Square 1 is 15 min away for me, the Milton Outlet is 5 min away, and I can still hit the old block in less than half hour
That morning traffic, from Milton to Yorkdale (for the few times Ive had to work out of the downtown Toronto office) can be brutal though. It is what it is.
If you aint fukking with Brown folks, Milton does have it fair share of Pakistanis. As long as it stays at current levels I aint too mad.
All in all its a long term project. If youre looking for nightlife or even a half decent eatery in your neighbourhood you wont find it. But in terms of school, quality of life, etc and bang for your buck its dope