This would allow us to complete the rehab using personal lines/private money and then set up traditional financing after 1 year of collecting rents.

Do you build slowly, and start with 1, traditional financing, 20% down, etc.?

Is it possible to refinance an existing mortgage into a FHA 203k loan on an owner occupied property and if it's possible does the property need to be occupied for the 1 year minimum like a traditional FHA loan?

Most traditional banks simply don't want to make a loan that small.You may need to do something creative like a private lender (friends family or associates) hard money lenders, owner financing or some combination of the above.

The current landlord has minimum expenses, and is treating the billboard as traditional commercial real estate evaluation.

I've been trying to find creative ways to finance a deal that I am analyzing and haven't been able to find an answer to this question: Can I use a HML to cover the rehab. costs of a flip and down payment on a house, while taking out a traditional mortgage on the property?

Awesome, thanks for your thoughts Christian!

If the property pencils out with traditional renters in all units, I wouldn't dismiss it too fast.

I have a few buyers interested in buying a fixer upper and they cannot get approval with traditional financing.

My guess is that if they're using traditional financing they haven't been at this too long.Hope that helps a bit, Best of luck,JTM