If you inspect 75 to 100 houses in your market (in a short time), you'll not only be an expert, you'll also find a great deal (you might not know it at the time, but you will stumble on one.)Best.

I'd love to give them a short-term out (we purchase the property from them by getting a mortgage after X months) and a long term option (say, 3 years).

Short answer, give a call to your contractor license board and explain what you want to do, it could be anonymous.

So for the short term, you need to keep enough funds to protect for any negative cash flow you may encounter up front.  

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As Dan said I would look into Airbnb depending on how short short-term is.

My (relatively) short term goal is to be financially independent by 35.

I visit and analyze the property, and estimate rehab costs (with experienced inspectors and contractors), add a buffer for unexpected repairs, and provide a financial model with an ROI comparison of a traditional rental vs. short-term rental.Any guidance/tips (positive comments only please) would be greatly appreciated!

I am 22 years old and just started working full time but my long term goal is to be financially free.For the short term I will continue to listen and read more books.

If I take a step back in the short term then so be it.