Got a good grasp of the concept, with very little info on the step-by-step actions I can take.  

You will be dealing with low-demographic tenants that qualify for S8 for negative reasons.

I understand the sentiment, but I think it will have more negative effects.The problem is with enforcement.

I would like to invest here but there are two large hurdles: Negative cashflow down paymentI feel that Boston is a fantastic city to invest in.....if you are well capitalized.

Should I focus on teaching him the basics of personal finance, like saving and budgeting, or is there a way to introduce him to more advanced concepts like market analysis? 

Hey @Robert Carmody, we are only on AirBNB and VRBO and they work just fine.I have been reluctant to do a Booking.com listing due to the negative reviews I have heard from other hosts.Booking.com was geared towards hotel stays, which means your STR gets treated like a hotel room.

Market your wholesale business as anyone would market a business concept and play by the Texas law and rules.

I recognize that the cost benefit may be negated by other challenges; hence, my question.

Sorry to be so negative, just wanted to point out some of the drawbacks of what you are proposing, I hope it is at least a little helpful.

That area is desirable and will most likely have negative cash flow for a while.