I don't think you're being too ambitious, I think its a very smart Idea especially in Chicago where there are an abundance of 2-4 unit buildings!

One good idea is to connect with the social worker department at the hospital to see if you can assist with anyone traveling to the area. 

The idea would involve working together to construct a road that provides access to my property.From there, I’m considering developing a 16-unit multifamily project on my land.

@Dylan Ray just south of you.https://www.biggerpockets.com/forums/521/topics/1225233-ocre...Good Investing...

If you think renting to her might be a bad idea, then do not rent to her.

I think all of your suggestions are great possible ideas to do this deal! 

I agree with the others here that say you need to have some skin in the game, if you are going to live there yourself, get an FHA loan rather than owner financing, you can get a 3.5% down loan, personally I do not love these as they require  PMI which is an additional expense, and you also need  bring additional funds for closing at least for taxes, title, attorney and transfer fees . borrowing from anyone else for the down payment, to include a personal loan from the bank is not a good idea, those again will be higher int. rate.

Quote from @Erick Pena: A "good" rental property is one that covers all expenses (mortgage, taxes, insurance, maintenance, property management fees, and any other costs) and still leave a surplus (commonly referred to as cash flow).Calculate cash flow as: Cash Flow = Rental Income − Operating Expenses − DebtThere's much more to it, but that's the basic idea.

To give you an idea of how we approach it, we assume the worst-case scenario right from the start is 9-12 months of no rent, $5,000 in legal fees, and an additional $5,000 in expenses to deal with moving their stuff, putting it in storage, and dealing with health code violations or NOV's from the city during the process. 

It is hard but as a realtor I pay attention to prices throughout the year so that I have an idea of whether or not it is a "real" discount.