It's on a deep lot, so I could potentially make it a flag lot, build another structure on the new lot and do both (renting to students and to vacationers).So, anyone speak the short sale dialect of real estate agentese who could help translate for me and save my pride?

A "live for free" house hack might not translate into a good deal when fully rented and, conversely, a good rental might not provide cheap living for the year when I am occupying a unit. 

This translates to the owner being motivated to offload the property for various personal reasons OR the house needing work (or a combination of both).

If I purchase a 300k house (3 bedroom) close to the Whitney Ranch Area, a 30-year loan at a 2.8% interest rate with 75k down would translate to about $1400 per month.

This spreadsheet translates that to housing price.

Yes that LITERALLY translates to that.

Put this under classifieds.Look on Fivrr for a translator you can pay when you use.

While not everything will translate to every city many of the concepts will help. 

Remember high cap rate on paper does not always translate to a higher total return or even a positive return. 

They think they got someone willing to sell their house for cash, that that automatically translates to a motivated seller.