The entire economy is based on real estate. It's a huge problem. It started being that way after Trudeau came. Back in 2012 you could afford a place in North York just by working regular SWE job. Heck, you could afford a place in downtown, albeit it would be on a smaller side. After 2015, the real estate just blew out of proportion.
Whether you buy or not is up to you. Personally, I wouldn't. You pay a lot of money for a place made from carton. Poor quality for insane price. Not worth it.
In regards to business. I will give you 2 explanations: tax and tech. cretinism in Canada. Every single bank in the USA would expose their API for personal use. Not a single bank in Canada would do that. To get access to it, you need to file a request, wait for 6-9 months, fill out maybe 30-40 documents, and then you can still get rejected. While in the US, you can just start. Taxes are higher on top of that when you start hiring people, they cost you more and they receive less; you have to pay things like EI. In the US, your employers will receive more money and overall will cost you the same. I am not even touching the investment and ease of building a startup. I talked to some people from the US and UK; both of those countries have way more opportunities to attract investment than Canada. It's also less bureaucracy, less red tape and thus, you can keep your OPEX to the minimum.
I have said it before and I am saying it now. Canada is not the country for people who want to make good money and afford good things. The tax law is set up in the way to punish you. The US is not for people who earn median salary; it punishes them but it's better for people who want money in life and thus, nicer things. The choice is up to a person. All this talk about "Attracting immigrants so they can build startups and hire Canadians" is wishful thinking. Anyone who starts doing that will realize sooner or later that it's like fighting wind; tiresome to get through so much stuff just to get very small output. There is a reason why there has been only a handful of unicorn startups in Canada. If one starts digging deep, one will realize that most money and investors are from the US and the company has an office in the US (physical or legal one).
I know you asked for success stories couple of pages ago. All of them will be from people like me. Those who came long time ago. Yes, I suffered in the beginning; my first job after CS at UofT was VBA dev at a small paper company in Kensington Market. The reason why I got successful was lack of serious competition. It's one thing to compete with 100 people for a position at Google, another one is to compete with 1000. It's one thing to live in a place and pay 1100 for a rent while your salary increases by 20-30K and another thing is face salary stagnation and pay for 2600$ for 1 bedroom. I gave a talk to the university in my home country and was honest about all of that. I wish people would stop listening to shady agents and do not look at Canadian immigration as the "land and get Benz in 6 months by working at Timmies".