In the investment world there are 2 main types of loans for us:  Conventional and Portfolio.Conventional - I'll define these as loans that come from Fannie Mae and Freddie Mac (if you recognize those names).

Generally speaking there are 2 main types of loans for investors: “Conventional” and “Portfolio”Conventional - I'll define these as loans that come from Fannie Mae and Freddie Mac (if you recognize those names).

That is entirely possible.And the loan that you can QUALIFY for will determine the best course of action here.Generally speaking, there are 2 main loan types for investors:  "Conventional" and "Portfolio"Conventional - I'll define these as loans that come from Fannie Mae and Freddie Mac (if you recognize those names).

If so, would the transaction I want to carry out with the bank be a genuine refinance from their perspective?

That way when you are ready to make your move, you can recognize a good deal AND you know what the normal houses in your market look like. 

If you max on your RRSP, you will be able to recognize a tax deduction.  

Any lease that I make with the roommates will not be recognized by the HoA according the above definition, but would be recognized upon a court of law (I would assume).

At that time, you really just need to start putting those ideas into action as knowledge unused is completely worthless.Self education is the key, but we all have a tendency to over self educate...... soon enough you will realize that you, in fact, are one of those "analysis paralysis" characters that you never would have thought would be you... meet with people, genuinely find out how you can help them, and you will achieve what you set out to do.Hope that helped man!

Generally speaking there are 2 main types of loans for investors: “Conventional” and “Portfolio”Conventional - I'll define these as loans that come from Fannie Mae and Freddie Mac (if you recognize those names).

If he or she has been doing this for any length of time, then your client probably recognizes that the odds of them staying for an extended period of time is low.