You're losing money if you paid all cash for these units.You doubt it? 

If he doesn't, then there doesnt seem to be a way to buy a property and not LOSE money.

She ended up taking a bit of a bath, and I ended up overpaying a bit but not having a kitchen remodel on my plate means that I don't lose a whole summer of rent and have huge headaches trying to do it long distance, so it all works out in the end.I settled on student renters for several reasons. 

If you boldly went under contract without an inspection contingency you will lose your binder payment. 

So, (assuming your numbers are accurate) if you sell you aren't losing money even though you bought this house a year ago.

On the one hand we would really like to clear out our debt we owe but on the other hand we feel we might be losing an opportunity keeping the home as a great investment.

This isn't HGTV...you'll lose real money if you don't know what you're doing and believe what gurus tell you. 

You lose more money on deals you dont buy.

I think what eased my mind a little is I make the purchase price number work for me enough that i can minimize my chance of losing capital.

The only time you truly lose is when you stop trying.