@Brandon Warren - if you convert it to a STR then you'd need to wait about a year to be able to use the rental income to supplement your DTI (since you'd need a schedule E showing that income).

I offered full appraisal gap coverage (property appraised at value), a 23-day close, limited inspection items to health/safety such as electrical, roof, radon, etc., and put down $10,000 in earnest money.

I know that I can claim supplemental charges later, but it's that much off?  

He worked his entire adult life doing manual labor .as he got older and acquired more health problems he slowed down and found himself competing with men half his age that could work faster And smarter .

What is a Health Hazard Eviction?

I've got a full time job and, for now, the rentals are supplemental income/retirement fund--netting 25-35K/year before taxes. 

Why would you supplement this Tenant's lifestyle just to keep them?

And it doesn't come with a steady paycheck, health benefits, or 401k matching.Last year I left my full time job to pursue real estate and other entrepreneurial efforts full time.

The downtown has a ways to go before it really recovers, some parts of it are likely better than others but I'm not on top of it because it's a segment I'm not interested in.There may be some interest in rentals in the south part of Calgary, particularly around the South Health Campus (new hospital).  

I’m in my 3rd decade as a real estate investor and my wife has had health struggles and we’ve homeschooled 4 kids.