A buddy of mine said to me a few years ago, "If the world started over how would you provide, you can trade stocks (I was really into the stock market at the time this was before RE) but that's useless, you wouldn't make it."

Don't want to be a jack of all trades, master of none.

Look at 1998-2000 or 2004-2007 or 2012-15, huge value swings in 2-3 years.

Rather than being a “jack of all trades, master of none”, you are controlling your costs, streamlining, and working efficiently.

[As you mentioned] what ROI is your local-Montreal market trading on?

As in having a tool in hand doing 50+% of the work themselves and hiring out a few trades (plumbing, HVAC, carpet, painting, basic demo help).I should also note I do not like my job and plan to leave in the next year. 

I'm in the trades and finding good cintractors is tough.

Even if I choose to buy my own place first in LA somewhere where I can afford, I will look out of state and/or turn key afterwards because I don't have the cash to make these big swing investments and I like spreading out my investments.

Residual income is the key, most people just trade money for time.

The prices can swing a fair amount based on the economy as these are second homes.John Corey