I'd focus on deciding what you want to do (flip-high risk, but potentially high return...or large loss; short term rental-more work, but higher return than long term rental; long term rental-less work than the other two, but lower return).Once you've decided which you want to do, then focus on getting the best house to meet your goal. 

EDUCATE YOURSELF - yes, it will take time, but will lead to a selection that better meets your expectations & avoids potentially costly surprises!

So, lots of challenges and risk but you could actually end up with a good deal.

Take your time, be wise, and time will reward you. agree 100%. you have people here on BP who have been in real estate for 20+ years and always talk about the risk and how hard it is - and then you have people who will tell you that after a weekend of a month you can make six figures in real estate. 

The restaurant going under is definitely the biggest risk.

A company that specializes might be a good idea, but if that isn't practical because the potential difference in taxes isn't that great it is something you can do on your own.

and i know that that there’s risk involved, so ill always be prepared for things not going according to plan. and i think starting small and gaining knowledge and experience over time is key. 

Hi there,I have a couple investment properties in Windsor Ontario, but am now starting to see where else to potentially invest. 

My point is, you are on the right track with your thinking, so now to the "HOW" to actually get in, if like me, you don't have an in or connection.First step is likely to get licensed, if you aren't already there are some other ways to get in the door and be helpful but licensed means they can pay you cuts of the deal and its less upfront cost and risk to them in helping you out.  

Plus, if the property is in a desirable location, you may have little trouble finding tenants.However, there are potential cons to be mindful of.