I have the ability to screenscrape data from sites and compile it but would rather just buy it from someone who has already done it. 

I'm sure they would love to help you and your ability to find potential leads.

However, as for dynamic pricing, you do have the ability to do this by just making rates different throughout the year and looking at what MarketMaker recommends for you.

Given that I have cash for a down payment and could get a loan for a "cheaper" house is it really the ability to come up with the money that holds people back?

I'm considering the wrap option so that this time frame could be extended and he could be free to go get a new car, house, etc... without this mortgage effecting his ability to finance.

Ultimately, it all boils down to you—your experience, your availability, and your ability to handle multiple tenants, units, and issues (trust me, they'll all come knocking).Typically, for beginners, anything beyond a duplex can be overwhelming.

This is an up-and-down duplex, and an unfinished basement with the ability to turn into a triplex.

I would get some assurance that her responsibility to pay the other mortgage won't impact her ability to pay her share of the rent.

Does the regime fee offset your ability to make positive cashflow.  

Just make sure you are confident in your ability to provide quality insight.