Last week the temperature inside my house was 21 degrees.

Have a steady job and live with parents saving every dime.

In the past year on the Oregon Coast we've noticed a steady influx of highly qualified liquid buyers from California explore the potential of investment beyond the Golden State. 

She gets a steady cash flow and you keep the land in the family.

As an out-of-state investor myself, my primary concern was getting an asset that would be steady/stable and had decent cash flow. 

The "resting" water temperature is roughly 55 degrees (the property is located in Northern California) Our average booking is Friday-Sunday with weekdays usually vacant.

Temperature, b. 

Obviously upside appreciation would be nice, but my main priority is a place to diversify some of my holdings (all in stocks, bonds, and cash right now) with real estate, while making a steady, reliable income from the property from the onset.

You would have to convince them that you could provide a steady stream of income for them, which might be difficult (see below). 

Neither of these are the Grand Slam option: which is to keep Indy and cash flow/break even on that mortgage while the home continues appreciating at a steady clip, and own 3-5 years in Buffalo....but this requires crazy good/forgiving terms on the loan-side, and the only thing he or I know of is the Doctor's loan.