This helped light a fire in me to start doing things on the side… Things that could create extra income that I could use to invest…Another key influence came from Robert Kiyosaki’s best seller, Rich Dad Poor Dad… (good one if you have never heard of it – jk).

I'm not sure if the mortgage industry in Canada is the same as the US, but 50k seems like a substantial enough income to cover a mortgage but i know they also take into account your existing debt-to-income.

One is a 12 unit apartment building, one is a SFH and the other is a duplex. 2 of his children (myself and older sister) would inherit the properties (partner on the 12 unit and individually own the other 2 separately).The other 4 siblings would get a cash buyout that we've all agreed is fair (and substantial).The challenge is how to provide the cash buyouts as part of the will and avoid income tax for the 4 siblings... notes below from lawyer. 

Will this be a substantial repair cost or challenge down the road?

I also did door knocking and use my sphere of influence etc..

I'd say use the higher price points in your market and build substantial amount of cash to invest into cheaper markets elsewhere, having a healthy mix between the two.Right now if you don't have the cash, find other investors and offer your time to rehab the property for their cash.

I've started the process of zoning in on target markets, specifically in more of the rural counties, as I found the competition in places like DuPage or Cook to be a bit substantial.

Not only could the inspector refer anyone to me for a structural inspection, but all the structural engineers I called won't do anything during the home buying process to influence or discourage the buyers decision.

The constraint here is that you'll need to achieve a substantial amount of equity in that year. 

I'm living as small as I can, so I can save a substantial amount to get things going.