My aim is not to waste anyones valuable time but simply to gain experience within the field.

or maybe I should be aiming for someone a bit more general that could also help with real estate law related questions down the line? 

The main reason we'd like to get into RE is to help supplement our income since my wife stays home with our 3 young children.

We are aiming to learning how to think about home improvements and updating, not as a homeowner, but as an investor looking to rent this home and soon hire a Property Manager. 

Costar has good data, but you'll want to supplement with local research (apartments.com, craigslist, zillow, etc).

Supplementing your tenants rent is charity not business.

For my personal property, I aim to have enough reserves to cover "a new AC unit" per property should all of our AC units go out at the same time.

@Cameron Oades Hi Cameron - there are a few markets in Quebec and Ontario (not the GTA) that I've been working in that still have great cash flow and moderate but steady increases in property value.I go for communities that show a 4-6% increase in value, a less than 10% overall vacancy rate (I aim for 5) and constant increases in population.I am currently working on 5 deals that are quite promising.

@Stone Jin - I will be ready to go on a down payment soon, getting qualified was my biggest concern going forward, speaking to a lender definitely will get me a more full picture.I watched one podcast that suggested aiming for 5 units in a year, and I wasn't seeing how the math for an average person works out, unless they are talking about properties for $30-$50k or so.

You will need to supplement your tennat $2500 rent out of pocket to cover the expenses on this property.