It is another to pay for a random coach who could be another student fresh out of the program.

I agree with @Thomas Fortune that you can do better elsewhere from a cash flow perspective, but vacation rental condos do offer many benefits, depending on your long term goals and personal use.

From that perspective I love the idea.

While Canada has no gift tax and Shahriar could technically "gift" any amount to his relative in the U.S.A. without tax implications at home - the transaction(s) would still be subject to U.S.A gift limits and taxation - he would not be investing at that point and could never "legally" accept any form of capital repayment {gift disguised as a loan} or profit from the gifted capital.The Canada Revenue Agency (CRA) takes an extremely dim view on loans disguised as gifts and, at their discretion, decide that the gift was really a loan or investment and treated as such from a taxation perspective.

An option buyer does not have such an interest.From the sellers perspective the lease option retains the strongest control of the property.

I'd like to bring in some fresh blood : >Joe, I pm'd you.

As of late, as I've become more interested in pursuing possibilities in the commercial real estate profession, I've begun considering co-working from an real estate investor's perspective (alongside satisfying, still, my original entrepreneurial interests). 

Just thought I would give you my perspective as a buy and hold investor working full time.

I would be interested to get your perspective.

That leaves you with a ~$15k down payment to the lender.Your seller gets the $380k, he pays off his $68k loan, and pockets the rest.This is only speaking from a finance perspective, and not at all to whether or not this deal makes sense from rehab ROI perspective.