Have 3 loans to refinance in the next few years and DSCR's are added to the option list.

That is the best option if you are truly trying to help a family member.you cannot get control of the mortgage, you can do sub2 but you are not in control, the bank could call it due if they see the property transfers title.The other way is for you to buy it from them at market rate, then rent it back to them at market rate.

You didn't provide that option.

I'm just starting out learning real estate, but I can't decide whether renting or flipping is a better option.

As already mentioned, he wouldn't be able to use rent from roommates to help qualify but based on the numbers you shared there should be a VA option available considering how much flexibility there is. 

You are limited in your options if something worse should come along later, such as a large investment going bad.If $10,000 CDN is a show stopper for you, how do you expect to manage a $600,000 CDN property? 

My opinion only 2 cases make sense for the seller 1) they have few options and this presents the best means to get out if a bad situation.  

Rank them from worst to best in capital expenditures expected*optional, not always necessaryAdd those numbers together for each property.

MTR may be a better option if not wanting to LTR. 

If it is purely and investment, then a LTR is a very viable option, as there is good demand for LTR.