For the multi-family, lenders typically count about 75% of projected rental income toward your debt-to-income ratio, which should help if the property is cash-flowing.

I took quite a break from buying properties and now on the hunt again.

OP ask your rental property insurer for Umbrella coverage options.  

I started my career with the renovations team renovating the houses we buy, and with the property management company working with our residents and our maintenance teams.

In real estate investing, financing is as important as finding the right property.

Does anyone know a well priced investor friendly property inspector in Calgary?

Managing tenants is probably the most frustrating task of all the task associated with owning rental property.  

If I sold, I think it would be by a hair that I can offload the property for the balance despite a tax value of $440,000, but it would get it off my books completely and free up my VA loan to purchase again. 

Historically, real estate markets perform best when the economy is stable, with steady mortgage rates and consistent demand for housing and commercial properties.

.#2 - Learn how to run comps so you know the value of the property better than anyone. #3 - Have finances in order (i.e) is this going to be bought through conventional, cash, HML, etc.