You need a legal professional who is tough when needed, wise and very experienced.Legal expenses are deductible against taxable income if you're structured properly.Then again, this is the type of expense you should only need to put out once.All that said, of course, it sounds like you need to be dealing with the local LLC-friendly banks. 

I have focused on minimizing my expenses so that my "financial freedom" number is lower. 

In Ontario, I find it hard to find properties that will cash flow at the 1%rule at the least when taking into account all the appropriate expenses.

It's not a problem with the concept of building a 2-4 unit property, the issue is all about the large capitalized expense costs vs. benefits.

It has to cash flow after all expenses or you're just buying someone else's money pit 

Specifically, they will be looking for capital for a down payment and operating expenses and reserves, capability to obtain financing in an amount sufficient to close the deal.  

I also write off the utility expense on my taxes.

But when it comes to starting a portfolio of rental properties, it gets really expensive to do so.

Rood and siding is in good condition, and the first major expense I see in the next five years would be replacing all windows. with a 15 year mortgage, at 5% (I'd rather budget high than low) cash flow would be 6056/year.

If you're seeing net $200 after all expenses then absolutely go for it.