We ended up buying the cheapest house in a upcoming neighborhood, so after capital expenditures I still have a strong cash flow. 

Accounting for all expenditures and being conservative with our numbers we will be close to just over 2,000 a month positive cash.

I have noticed a few of break-even properties (after Capital Expenditures) that interested me within outer cities like Hamilton, Guelph and Barrie. 

You are missing on maintenance, management, and capital expenditures.

You must be able to pay property taxes and insurance, plus capital expenditures (a bit of money set aside to replace things that you’ll need over the next few years, such as roof, AC, water heater).  

Besides loss of control over when and how you make capital and routine maintenance expenditures, there's additional insurance you need to consider.For example, if someone seriously injures themselves within a common area, and the judgement is over whatever liability the association carries, YOU will get assessed your share of the extra dough.

We at least aim at paying off our mortgage and other expenditures connected with the cabin.

Cost of Holding: Buildings eventually need repairs, so getting out before all the capital expenditures hit you at once.

We recently replaced a roof on a property in TN and were more at ease with the large expenditure based on something that @Luke Carl said: this is a long term investment for generational wealth.

This wasn't much of a "value add", but it will decrease Capital Expenditures after closing.