I don't "need" to see the cash flow in Year 1, but appreciation is a ton more risky - and I'm probably worse than the average person in anticipating RE cycles, hence a mix of CF and appreciation is desired. 

The successful ones, though, have met with professionals and fleshed out a plan that anticipates the ups and downs of a market so they can see the good and bad without losing their shirts. 

We anticipate a mobile app in the coming months.

A buddy of mine sold his house 3 years ago and moved his family into an apartment in anticipation of another GFC-like crash in housing prices.

The data interpretation would be useful in a few ways I would imagine.For example, analyzing traffic and usage patterns for vehicles and common usage areas would be good to determine the anticipated lifetime of the asphalt parking lot and if sidewalks or walking paths are not being used and why. 

@Orlando Osuna - Sorry to hear...are you getting any rental income, even we have similar situation all the rents from new tenant are constantly going for repairs (100% of them) - we are paying out mortgage out of our reserves and had to borrow from one of our private lenders with higher rate) as we never anticipated we would not make any $$ for almost entire year. we are in a deep hole :( on this one. but hoping to sell if we can get decent rate on our unit...hopefully next summer if we get good offer we will be selling it for sure.

However, there are major developments going on and I anticipate there will be a steady increase in appreciation on the island in the not too distant future.  

MFHs are very hard to find in the area, so I wonder if that would allow me to still be able to assign it even if the discount is lower than anticipated.

While you will find lots of information and experience in these forums, keep in mind that while much of it has universal application, some is very U.S.A. specific (particularly in the areas of finance, regulation and taxation).Case-in-point are the calculators on BP - while they can be a valuable tool even for a Canadian investor (though the buy-and-hold calculator misrepresents vacancy and mortgage principal as expenses), you would need to know how to "adjust" the financing side to align with mortgages in Canada.As far as jumping into your first acquisition, you are close enough to the Big Smoke that I would anticipate real estate prices to be very full in the Orangeville / Purple Hill area, so taking your time to educate yourself and be comfortable with the process is not a bad thing.

Prop A seems like a good long term place and if it appreciates as much as you anticipate in the next 5-10 years, you could use some of the equity for the roof and still have equity left over to possibly put down on another property.Edited to say: Prop A currently looks cash flow negative.