She has basically asked us if he can move in November 1st and has already assumed it would be fine with us…We are not comfortable with the situation and are trying to figure out what our options are.

This is the long way of asking - is there a place to sell by the owner and offer a discount for a quick settlement, if maximizing my cash return isn't my first priority?

I've done several on my own but some people are not comfortable.

From your post it sounds like you need a good tenant in there more than you need to maximize every dollar.

It's way too common for Landlords to get too comfortable and chummy with the renter/handyman.

It sounds like they are coming from a place where they don't know nearly as much as you about rentals, so it's your job to teach them in a way that makes them feel comfortable.

Such as things you wouldn't be comfortable talking about here or elsewhere.

But not maximized.

Here are a couple pieces of advice I have for you or any new beginner:Start investing as soon as possible, not as soon as your comfortable. 

I do feel comfortable finding my first deal because I feel if I do get a mortgage from my bank I would end up paying high interest.