The challenge with out of area is lack of local knowledge & difficulty managing from a far.

I'm having difficulties finding a lender that would do a cashout refi on a property I just rehabbed

Without giving them any type of written warning for these issues, you may have difficulty making them leave if they challenge it. 

If you have the house first, only you have skin in the game.

The older couple have only been dating a year, and despite the length of the lease, and their income, I suspect if things went south with their relationship, or some of their legal difficulties, I think they'd be more likely to try and wiggle out of the 2 year lease. 

@Anas B. drop me a private message, if you're still having difficulties finding someone.

I am having difficulty finding a buyer with a multi-family home, instead I am hearing that they do not want to deal with the "nightmares" of selling to an FHA loan.This has thrown a wrinkle in my initial plan.

At this point your realtor has got some skin in the game.

How difficult is bank financing when it is out of state?

The difficulty (but fortunately the one you as the broker or investor have control over) is the location of the new property.