Option #1 will most likely meet that criteria, you can price for any major repairs/cap x improvements and negotiate those during the acquisition, this will help you hedge against major items breaking down once you acquired.   

Unless the condo is an improved living situation, you'll have some trouble getting owner occupied financing

As soon as we walked through the house it was pretty easy to figure out how the kitchen could be improved.

With improving investment economics, is Montreal one of the last markets to see real value for multi-family properties?

According to the National Association of Realtor®'s 2016 Profile of Home Buyers and Sellers, the average FSBO sales price was $185,000, while the average price for a home represented by an agent was $245,000.

But the property would never do that because of its design and limitations, so in order to make money, I'd have to either create more space/more bedrooms, or wait for the area to improve.

Getting my profile up and running and looking to participate more in the forums.

Here's his info: https://www.trulia.com/profile/clayton-pickens-age...Hope this helps! 

For me, I'd like high cash flow with opportunity of improvement and sale in 3-5 years.

I was baffled at how your successful career was spurred by something as simple (yet difficult to commit to) as self and lifestyle improvements.