I've personally found the bulk of my Chicago purchases off the MLS.

FidelFidel,When I saw your question I got interested as most Canadian investors are rather running away (or pausing) from investing in RE in Canada.But to help in your journey, here's what I can share mostly from either my personal experience or discussion with relevant professionals. 

It sounds like a single family house where you will be living in the house(personal use).Therefore, you may not be getting the tax benefits you think you are.Consult an accountant.I am not sure why your sister would agree to this as well, she is losing $170,000 in this transaction and she faces the possibility of you increasing her rent.You also have to charge market rent or close to market rent or it is all deemed personal use.

The first is having a personal portfolio of 5 passive rental properties, not including my residence.

Quote from @Adrian Lammersdorf-Scioll: I'm helping a buyer right now that works int he hospital get 5% funded for them on a home, that may be something to look into, it's called hometown heroes here in Florida.  

I am 59 years old, and my retirement fund is all in my 401k.

Then find out from the person on title, not the assignor, what the assignor promised or has in writing as an agreement.

Personally I consider it to be more of a entry level neighborhood for first time home buyers and a blue collar neighborhood for long term renters.

I personally want to learn from those with experience.

He personally screened every tenant, handled every maintenance request, and even showed up to mow the lawn at his properties when the landscapers were running late.His phone rang constantly—contractors, tenants, vendors—all needing his immediate attention.