Your best bet is to network, speak to friends and family, and hope someone you know has past experience with what you're trying to achieve.

I'll possibly be buying a new personal residence in the next year and look to rent out my current home and I do expect the lack of rental history on this property (despite having my other rentals) to negatively impact what a bank will approve me for, fortunately I'm not trying buy a million dollar house so I expect I'll still be okay.

Even on the low end of that, 40% means you're really only bringing in $1035 out of that $1725, which means you're cash flow negative.

When I buy my new house and rent out my current home it will be negative cash flow.

But I am considering purchasing her house from her and then she can pay me what she can afford every month.I have two questions.1) Has anyone ever purchased a house and then rented to a family member, if so, has that experience been more positive or negative?

In terms of getting in contact with someone in the city to speak to if further questions arise, is there a number or contact that you have had the most luck with?

I'm also looking to seek counsel with a CPA/property tax attorney... would that be the right person to speak with?

@Eddie Egelston that was great "food for thought" as you say , like the way you put the numbers out there and let it speak for its self. 

Wholesalers only look out for their best interest, generally speaking.  

Look forward to speaking some time Alex