I am not an expert on va loans but I question if the lender will permit a 2nd primary residence in same vicinity as the existing primary.  

Looks better on paper, no carrying costs, lender points, etc.

If you finance it, it's much longer - IMO, you lose another 25% of the financial ROI, with the only ones making money being the installer and the lender. 4.

DM me and I will send you contacts for; attorneys, lenders, and accountants they have previously used.

I haven't done this but I don't think too many sellers would want to do this and if many lenders are agreeable to this set up. 

@Quincy Mingo I'm a local lender in Chicago and can help you navigate this.

Did you work with any real estate professionals (agents, lenders, etc.) that you'd recommend to others?

Ian -I don't think there's a one stop answer for this as I haven't fully studied your situation.In addition, the IRS has specific rules regarding loans between family members, and there are tax implications for both the lender and the borrower.The IRS might impute interest on the loan, meaning they could assume that interest was charged even if it wasn't.

One would need to connect with a realtor, lender, there's inspections, there's needing a specific amount of capital to invest, tenants, property management, etc. 

So I would like to to connect with lenders, construction contractors, and partners, for the local area first and beyond in the future.