If someone is willing to live in and renovate the 2 of last 5 year capital gains exclusion is a significant consideration.

They just live T get you to apply and paper appraisals.

Smaller SFH = less maintenance , there are lots of single looking for a place to live .

If there's a hole, it may be a red flag.b) sensitivity analysis: I examine all the assumptions, and make sure I can live with the worst case scenarios.c) "Stall and see": if they are getting money over multiple years, and there is no penalty for investing later, I would usually wait so I get some real performance data, versus having to look at theoretical pro forma information.d) Recession stress test: I will not invest in anything, until I subject it to recession level stress and see if I can live with the result.

My mom lives in a nice house that she has paid off.

It's not a bad strategy, especially if you live in a lower-priced area with a good rent-to-purchase price ratio.

I specialize in working with Canadians that own property down here (I live in Palm Springs, we might be the snowbird capital of the world?).

No, not places you heard people want to live, or were told, or think, no-no-no, where you KNOW people want to live. 

He wants to live in one and use the other for his studio. 

But it’s clear you’re a smart investor who knows the long-term benefits real estate can bring.I keep reminding myself why I stick with real estate: you can make money every month in four different ways:Cash Flow – Passive income to live on.Appreciation – Long-term property value growth.Depreciation – Tax benefits that reduce your taxable income.Tenants Paying Down the Mortgage – Even if you’re paid off now, this is one of the biggest wealth-building tools for leveraged properties.It sounds like your main struggle is the stress of active management—and trust me, you’re not alone.