I’m thinking about building apartment complex in phases mainly due to finances.Question re refinancing.

You need a new agent, one that specialized in investment properties and that specific neighborhood.  2-4 units in Chicago can be very complex so make sure you find someone with lots of experience in them.Also, do not look at Zillow. 

The housing prices there have also skyrocketed, however; there is a whole bunch of apt complexes being built up now that might eventually balance out prices.I've never bought anything down in Chatt, but all of my investor buddies say it's a great place to find good rentals.Let me know if I can help locally in Nashville and the surrounding areas. 

Is my profit margin goals to low/high2. should i buy and hold every other house or two to start building cash flow now or just keep flipping untill i can roll on a 'big' complex or something3. 

You need to learn some basics before moving onto such complex transactions. 

If you do want to get involved in some calculations you could try to figure out the time value of money against its current net worth with the income the home is generating.Or ignoring the complex math problems, a good rule of thumb is if you can make 10X the yearly cash flow when selling, consider offloading the property and investing in another.Cheers! 

@Henry Der now you have added the complexity of Canadian taxes.

My current situation:  Renting a 2bd/1ba apartment in a garden-style apartment complex. 

But if I was to go the single complex approach I would like to rent that out and make a little income out of it nothing crazy I just want to get started in the game .

There are certainly some complexities such as exposure to taxable UDFI (unrelated debt-financed income) on the leveraged returns.