Hey @Jake Wosick - You should definitely connect with @Zach Shepard above, he's been a great mentor for me and knows the off-market chicago space better than most.In my opinion, the key to off-market deals is understanding the ROOT issue with the seller. 

I am currently studying for my real estate license and analyzing the local market.

Study the market.

I know Austin; I don't know other markets.

For those that are in the MTR space, what types of clients are you targeting?   are your getting traveling nurses, business professionals, displaced families, insurance claims etc?

You can't arbitrarily decide that you don't want to allocate any of the proceeds to the portion of the property that will create Ordinary income recapture (thus can't be included in the installment sale treatment) - it should technically be allocated amongst all the assets in accordance with their fair market value at the time of the sale. 

There are several online marketplaces for purchasing digital businesses.

Recently I saw the duplex that is DIRECTLY across the street from my property come on the market, and I would love love love to jump on the opportunity to buy this property as well. 

I'd build on an infill lot closer to downtown. you can get land within the downtown markets and construct multifamily properties through the same process and higher units and better floorplans. we just passed our first triplex in central ohio and are breaking ground in 3 weeks. 

SF houses are easier to maintain, have greater appreciation rates, and appeal to a bigger buyer market.