Everytime I look for Multi-family it either seems over priced or non-existent.

If she doesn't qualify on her own, or if it's too expensive to refinance a bunch of properties to achieve the goal, then it's time to start with commercial, non conventional, no income verification loans. 

Non-negotiable.

Most people in that area or DC or any of those, that I've known at least, tend to invest non-locally so they can get cash flow.

If the shop building or remaining 15% do not add value above and beyond your cost then I suggest protecting yourself with a non-refundable deposit or some other assurance from this buyer.  

So I know a lot of people here read realestate and business books. I'm curious if anyone reads family books to better relationships or parenting books. If so any suggestions would be awesome.

If there's a public school across the street, is it a plus or a minus?

Hire a competent consultant or accountant(non-cpa) to review your books to see what you are doing right/wrong. 

I've never lived in Orlando (only been there a thousand times) but it seems like there is a non-stop flow of new vacation rentals and timeshares. 

What's the difference between an educated seller and a non-educated seller?