In the Montreal region it's not easy to have a positive cashflow while occupying a unit, but at least it decreases your cost of living. 

I thing the HELOC route is a good one as it allows you to continue acquiring properties.Have you taken the time to sit down with some local/regional banks/credit unions and talk through your plans?

I am unsure if this is a good region but I'm going to investigate more. 

If you have income, assets, and credit, you should have no problem borrowing from a local or regional bank (not national) for rentals and flips.

However, for a rental depending on the region of the country and the type of rental you might consider not adding AC. 

In the more desirable part of US like coastal regions, homes here have appreciated 2-2.5X last 5 years from the trough to nearly peak.

How many of you have purchased property sight unseen, either in your local market, regionally, or out-of-state?

One of the biggest things to consider is your comfort level with the longer term macroeconomic outlook of the regional / city economy.The other major consideration in my opinion is where you are at financially,  in terms of goals, and where you're starting from financially. 

Hello BP folks,Can anyone recommend a good real estate attorney in the Hampton Roads region? 

I'm in education mode but afraid i'll get stuck in analysis paralysis and waiting to market time  and trying to find the "perfect" market/region...