But, could I minimize risk of renter defaulting on payments for the 2nd property by turning this property into a section 8 housing unit with guaranteed income from the gov't?

Quick info on me that could possibly help: Licensed realtor, good credit, first rehab I’ve owned but not the first flip project completed by the GC or by myself as the realtor, strong W2 income in addition to real estate.

Does anyone know of any local Winnipeg meet ups or online Canadian Real Estate communities?

My siblin has a credit score in the low 600s and Annual income of $40k and my credit score is in the 785 range with annual income of $170K.

:(    Owners just do NOT have enough stress:  under water, extreme deferred maintance,  loose of income and behind on payments. 

If you embrace the ability of real estate to replace your current W2 income job, this could be the first step toward doing that.  

Make sure you're performing credit checks, background checks, verifying income (calling employers and even checking bank statement if you need to), and calling former landlords to inquire about/confirm their habits as a tenant (cleanliness, respect for neighbors, paying rent on time, etc.).If you don't think you're capable of this, definitely find a good property manager!

I live in an area with very large incomes, and low house prices compared to the rest of the country - there's dozens of cities and towns in Canada like this, so don't paint the market with a broad brush. 

I was reading online and saw that FHA Loans accept auctioned homes but that got me thinking.

maybe re-verify the couples income to make sure it meets your rental income criteria.