You can get up to 75 LTV on a 30 yr fixed based on property cash-flow at 4.5% - 4.875% but not sure how that compares to what you're on now. 

My other strategy, which seems way too unwieldy and unfocused, has been to open Google Maps, and pick random cities that I have either heard of, or are adjacent to population centers or natural attractions (mountains, lakes, parks etc), and start looking at Zillow and comparing historical data for the props I see listed to try to gauge where we might be on the bell curve of appreciation.

High price, normally not great condition, and rents so so low compared to purchase price....like $1000-$1200/side on $400,000+ purchase price. 

If you don't research, you'll likely not notice much of a difference in how the lending process goes compared to personal mortgage loans.

Mind you, people have found properties that way and some have been happy with it but they'll never know that there maybe or even likely was an even better property at a cheaper price.Speaking of price, working with a single realtor's inventory means that you'll probably have only few comparables, if any.

QUESTION #4 Would it be a smart decision for the tax purposes of losing our personal home deductions in our taxes compared to the benefit of depreciation and others tax benefits with the LLC.

That may have caused small multis to look comparatively less attractive, when that is not necessarily the case.

Seeing as this would bring a great element to anyone vacationing to MB looking to stay in an Airbnb. 

Halifax NS also has "affordable" prices (compared to GTA) but I've found recently enacted regulations to be much more tenant-friendly.I would love to connect and hear your thoughts and experiences!

I relied heavily on the PM to determine the rents, but we also used other RE tools like primary MLS's and Prop-stream to pull comparable rents in the area.