We both still work full time and will for the next seven years barring our health stays good. 

As far as the older heritage buildings go, yes it’s a pain dealing with the heritage bylaws and you’ll have to increase your budget to redevelop the older buildings to bring them back to their former glory, but it’d be difficult finding a better unit once they’re complete.

If your employer is paying benefits like health insurance, retirement match, dental, vision, disability insurance, etc. increase your $40,000 salary by about 25% to cover that part of your compensation package.Real estate agents follow the 80/20 rule.  80% of the commissions to 20% of the agents. 

Despite this being a pain in the neck, I'm taking it as a positive as its giving me more experience. 

It sounds like your broker was the pain point.

Landlord tenant law is heavily skewed, taxes are high, drug use is prevalent, the buildings are OLD, and it can be a pain in the *** to find tenants.

You need to look over the financials, the budget, and the reserve study to understand the financial health. $125 sounds about right or possibly low. 

I could have used a property manager on those properties but lease up fees of one months rent are painful when rents are in the $1300-1500 range. 😬 My goal is to eventually leverage all of our SFR equity into multi-family properties, and manage the managers of those properties, not the asset/tenants themselves. 

It adds another level of negotiations and is a pain for sellers. 

Wonderful news about your son's health.