If the interest you're paying your father or someone else, combined with the interest on the mortgage, combined with the principal paydown, the rent received, the expenses... if everything results in cash flow that meets your goals, then it will all come down to mustering the faith to take that next step.I would highly recommend connecting with someone locally who has house hacked... pick their brain, learn how they made it work, etc. 

If you're looking at single family homes (SFH), the best way is to look at what has sold in/around the property that you are trying to determine the value of (preferably within last 6 months; location dependent).

Chad,I strongly suggest you review the By-Laws of the Association to determine what parts of the Building you will own. 

I have had folks hold on to our letters for YEARS and call us when they finally determine they no longer are going to use the property.  

The other caveat is that your credit score will determine the LTV as well as your ability to service the debt.

However, I have determined to stop letting deadbeats get away with it.

If you are planning on investing in the States (I deal with this all the time with Canadian investors here in Arizona of which there are plenty) they overlook talking with their chartered accountant before determining the entity they chose to purchase under.

Looks like I can pick up single family homes for $50k or duplexes for $100k.

Its best to find your own comps to determine value.

The areas where students live have been picked thin by investors for years.