Alternatively, OHFA's down payment assistance might work - not sure if it allows for duplexes.

i fyour getting paid off when the vertical loan goes on.. then your in first position . so not sure what the issue is? 

I’ve been in real estate and mortgage for over 30 years, and if there’s one thing I know for sure—it’s that there’s always more to learn.

I would make sure your numbers are solid and that the deal would make sense and is lucrative for the investor. 

Sure. 

An eviction is a last resort, but also want to make sure I’m fully aware of the landlord/tenant laws  Yes, I believe all laws in all state say that. 

I would like to make sure the siding is presentable before paying for an appraisal.

Make sure that is tight.

I'm sure there are more FHA loan experts on the forum, but in general a borrower can only originate 1 FHA loan at a time since they are required to list the property as their primary residence and live in it for at least 1 year.

I make sure that when I am doing major work that I plan to avoid potential problems on a Sunday. ie I am not replacing valves and faucets on a Sunday in case something breaks and I need to shut off water and go get a new part to fix it and they are all closed until the next morning.