If you are planning to do estimates sight un-scene using square footage I would suggest your increase your amounts. 

Outstanding loan principle: $139,900.

Then planned a move to South Carolina and bought a house sight unseen for $44k to renovate and live in. 4 months later (while still in Canada) the house across the street from my dad came on the market so I bought that one sight unseen to renovate (better area) and decided to rent the first one.

I have a neighbor who bought their house “sight-unseen” from China before moving here permanently.

My local community colleges offer courses in Real Estate Principles, Practices, Finances, Investments, & Legal Aspects of Real EstateDo these courses offer any benefit besides fluff knowledge?

This usually happens when the objective is to lower payments or escalate principle pay down and take advantage of a lower interest rate. 

We understand the concept and principles and the outline of assignment contracts but I definitely need some help in the area of what should first?

You can deduct interest payment not principle, can claim depreciation and also may qualify for energy credit. 

Follow up on tax sales that have not been foreclosed - some fat equities there also.Attend some of my real estate auctions - some good deals there.Make many offers - sight-unseen subject to inspection - do this right and it will accelerate your success in this crazy business.

Sounds like you have a good grasp on that, but a lot of people lose sight of that when choosing an agent.