I won't be investing in the riskiest/most supportable asset subclasses such as hotels, and tilt my portfolio the ones that have historically been more stable such as multifamily and single-family housing.

We all eventually come to realize that contractors have a shelf life.

If you just want steady and stable cash flow for income replacement, you might put a little more weight on option B. 

I am aware that mutual funds can be good as well, but I do not feel comfortable putting money into the stock market. ( I know real estate markets can fluctuate but historically aside from the crash have been relatively stable and increasing at a consistent slow rate )2) I have two sisters but I will be the one to take care of my parents when it gets to that point in life and I want to be sure that money is not an issue when it comes to getting them top shelf care, if needed. 3) Real estate gives me motivation that is long term rather than a project at work that is not infinite.

The rental credit keeps your Debt to Income Ratio stable since the rent washes the mortgage debt.

A stable cash flowing rental property.

But if you buy 5 with 20% down each and you get hit with that same roof issue, it is likely some of the others won't need as much capex as you budgeted for that year so your overall return will be more stable.

I am wondering if I just have to pay almost full price if it has a good/stable rental income in a great location to start.Any good advice will be appreciated.

Unless its an old school bear claw tub you need to put supports under the tub because the new claw legs aren't stable. 

Montreal is considered a stable market and so the CAP rate has been traditionally low, at around 5% (it's actually closer to 4.5 as the market gets hotter and hotter).