You know this but how you negotiate the deal is listening to your seller and seeing where you can take the price. 

I’m assuming the person flipping would probably have to have an extremely great deal or partner with someone who’s done this before?

its not guaranteed until the title commitment is done and in hand.. lenders want that a few weeks in advance so they have time to review it and check that there is nothing on title they dont like or is a deal breaker to funding.. they dont want to do all the work then have one day to review and approve title. these companies work just like a bank  they have set process's and getting title commitment and funding  same day is not one of them. now myself I will without title insurance.. and rely on a trustee's guarantee and my borrower if something does not go right then my borrower has to make it right.. so it takes a very special borrower that has that capacity.. and or have earned my trust.

I believe I can demonstrate that the property was originally used as a two-unit dwelling, which could strengthen my case.I want to ensure this deal is still viable and that securing the proper permits is realistic, as my financial projections are based on this being a multifamily property.

The only thing I can think of that may be harder to deal with if I am not local is routine maintenance issues, but I was thinking I can just ask around for some handy man referrals to have at the ready in case those smaller issues arise, while I would instruct our future tenants to contact our service provider for any emergency issues. 

I've been investing in real estate with my wife since 2017, when we started with JV deals and small flips.

Id love some input on starting my own property management business to generate cash for more deals.

When you can buy properties like this, you can get almost 100% of your money out of the property, convert the property into a long term rental loan, with a DSCR Loan (Debt Service Coverage Ratio) where we as the lender look at the property and if it cash flows, and that is expressed as a ratio, for instance if your Total Loan payment including Principal, Interest, Taxes and Insurance was $1000/mo, then you would need a rent of $1200/mo and you would have a 1.2 DSCR Ratio.Here is an example of a cheap duplex https://www.zillow.com/homedetails/732-Broad-St-Menasha-WI-5...

Is it more because of a borrower not qualifying traditionally, property not qualifying, or they can get a better deal going private?

It was more to have another cool place to vacation and let it pay for itself and appreciate.I never plan on selling either property.If I see a great deal on a beach house that will be next.