Timing any market, whether it's stocks or RE is not something I'm willing to bet on. 

Yea it looks like hold or sell and hold Canadian might be best bet it looks like.

Unless you want to bet on continued appreciation,  why keep something that losses money.  

I have seen a few places that divide the utilities according to square footage or number of occupants for the water, but I would bet this opens the door for neighbors to be complaining about each other and insisting they are using less than their share- I would rather avoid that issue.Good luck with your decision!

Obviously we want something we could "force" appreciation into with updates, as opposed to betting on the market.

Not all my relatives are reliable and trustworthy but my siblings, grandfather, and these uncles are.I don't like the distance this place would put me at, but I think eventually when my grandfather inevitably passes, (and when my siblings and I find spouses), I could move to a more central location and rent out and manage all the houses (which at that point would be 5 sources of rent or more).Is this a realistic idea?

hey Account Closed, i had the same idea once i saw deals were not easy. then again, nothing good is easy. my advice to you is don't go it alone, but try to minimize yourself getting cheated... next piece of advice is this: don't buy just a condo yourself, and then expect to buy investment property. your next property, if it's within 2 years, will be considered an investment property, and you will have to put down 20-25%, otherwise wait 2 years. i don't know your situation and life story, but also, it would be much easier to find lenders going from a 2 family to 1 family, than a 1 family to 2 family. as for stocks, i'm into the long game, so Vanguard ETFs, indexes are the way i go. warren buffett has a bet going on with a hedge fund manager; 1 million dollars to the charity of choice if the s&p 500 outperform the top 3 hedge funds of anyone's choosing over 10 years. someone took him on that bet but warren buffett is winning. 

I need some trustworthy regular guidance or this is never gonna work.  

Your best bet might be to work with an international bank with presence in both the US and your country.

Your best bet is a LOC or something from a bank.