As for my Airbnb research, I have spoken with a person who runs numerous Airbnb’s in a different area (city atmosphere) who provided good ideas on how to smoothly run the property.

FHA 203(k) Loan BasicsThe FHA 203(k) loan is an excellent option for financing a multifamily property (up to 4 units) with only 3.5% down.

In my case, I think TK is the best option - at least to initiate my real estate journey.

It just obviously won't be market specific.On a personal rezoning I did for a house hack new-construction triplex, I was asked numerous questions about how many bushes and trees I was going to plant.

Stocks again can diversify (and frankly I don't see the benefit in investing in real estate related stocks - there are much better options) Are there any tax benefits?

Sounds like you have some interesting options, and good reasons for both! 

Option 3: Find a better investment at this time.Stop thinking of yourself as a real estate investor and start thinking of yourself as a well rounded investor.Pay off your mortgage: Your money is not working for you when you spend it on liabilities like a personal residence.Buy Rentals with little/no cash flow: You are speculating what a rental will be worth in 20-30 years.

If you ever need assistance or guidance with financing options for your project, feel free to reach out.

One option I'm considering is adding the equivalent of a camelback, or second story over one side of the home, adding ~900-1000sqft and 2 or 3 bedrooms. 

There just aren't a lot of options in my area, and my kids need to live close to their dad.