We have made money buying properety based on cash flow (lower priced) rented out for a period, then selling to an owner occupant. 

I tried calculating value based on NOI and cap rate (see below) but I'm new to this and the value seems to come out lower than I would expect.

The numbers may be 30-40% lower than today's cost, but the process/approach to estimating may be good for you to review.

Consider lowering your asking rents before changing PMs.

By having a higher credit score or lowering your LTV you can reduce your interest rate and help to increase your DSCR.3.

Your PSF will be much lower than it would be adding one small unit per lot.One thing to note is more than 4 units or more than one ADU changes the financing that is available.  

Have you lowered the price at all?

The tenant pool can be lower end in Winnipeg but if you invest in the right areas it will often qualify for CMHC financing in terms of affordability. 

I have focused my research on house hacking due to the lower upfront capital requirements with an FHA loan.

that we’ve learned in our 24 years, managing almost 700 doors across the Metro Detroit area, including almost 100 S8 leases:Class A Properties:Cashflow vs Appreciation: Typically, 3-5 years for positive cashflow, but you get highest relative rent & value appreciation.Vacancy Est: Historically 10%, 5% the more recent norm.Tenant Pool: Majority will have FICO scores of 680+ (roughly 5% probability of default), zero evictions in last 7 years.Class B Properties:Cashflow vs Appreciation: Typically, decent amount of relative rent & value appreciation.Vacancy Est: Historically 10%, 5% should be applied only if proper research done to support.Tenant Pool: Majority will have FICO scores of 620-680 (around 10% probability of default), some blemishes, but should have no evictions in last 5 yearsClass C Properties:Cashflow vs Appreciation: Typically, high cashflow and at the lower end of relative rent & value appreciation.