New investor in Mississauga—where to even begin in this market!?

[Doug Findlay]

I'm brand new to the REI world, stumbling into it after hearing a comment my stepson made to my wife: "Why does your generation only focus on being mortgage free?" My first reaction was to dismiss it as 20-something idealism fueled by get-rich-quick TikTok and YouTubes. Of course the more I look into this, the more I kick myself for following in my parent's footsteps: save up to buy a house, pay it down, live within your means and call it a day.

So we’re motivated to start but it seems to be a terrible time to do it…at least in the GTA.

So far I have about 36 hours of experience in this field reading and watching various webinars etc. lol so looking for some advice. We have a home in Mississauga valued at approx $1.4–1.5M with 380k remaining so I could secure likely somewhere north of $750k to get started.

My thinking is to get financing established through a HELOC so that's ready to go and I'm not a much of a gambler so I'm not looking to invest in cash flow neutral or negative properties and hoping for appreciation. This seems to leave me looking for my first cashflow positive property but that appears not to exist in the GTA.

I always imagined landlording property nearby—you know, in case a faucet starts dripping and I need to run out there to fix it. LOL :-) I see a lot of investors buying exclusively from a distance and using a property management company to do the legwork on the ground. Are there perils to consider looking far away / out-of-province? I also have family in the States—is there any advantage to using them to buy down there versus going it alone as a Canadian citizen?

Any helpful links/advice/tips/contacts/suggestions would be SO much appreciated. Thank you!