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? 

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. 

Something else to keep in mind is a LLC does not provide absolute protection so you still need to take other measures to protect yourself like insurance, umbrella insurance policy, trusts to help further hide your identity, don't use your name and home address as the registered agent for the LLC. 

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.

I get calls all of the time from agents who have buyers that want to "Just measure the curtains" or "Wanted to see the Basement again to see if a pool table will fit" or "want to count how many energy efficient light bulbs they need to buy" or "To see if their camper will fit in the garage"The answer is always the same "I'm sorry we are unable to accommodate that request due to everything going on at this time".

@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.

Bring a measuring tape?

As a stop gap measure until you can get it on the market to sell may work but you definatly do not want to hold on to this property for long. 

You eloquently described what I was aiming for - intellectual liberation, development of social and intellectual capital and ability to critically think (in some cases).