There are way better and safer things you can do with your money.

Give him 60 days to sell or refi the property.  

From the little I know of San Antonio (I am a wholesaler who specializing in selling STRs nationwide) its not a super hot Airbnb market but the amount you expect for rent sounds pretty conservative. 

Some people seem to get locked in to one place they find, or a place a friend or family member is selling without really evaluating the available market.In a small town in East Texas I would think your biggest risk is a big player coming to town that can absolutely crush a smaller player. 

My thought is that the people that ARE using it for lead gen/outreach, automation etc. will keep the methods to themselves until the advantage of early adoption is done and that business segment is saturated, then they will sell courses to everybody else..

Does anyone know, or have a good idea, about the difference in returns on entitling & developing the land for each scenario, with final objective to sell to a builder to build and sell the structures him/herself.  

It sounds like you will not have lived in the property for 2 out of the 5 years immediately prior to selling it. 

It is sometimes better not to sell to this buyer than deal with the year long headaches that follow.

Are you looking to just subdivide and sell the lots or actually build?

I FOUND THIS DEAL THROUGH WORD OF MOUTH I WAS TELLING DIFFERENT PEOPLE IN MY CIRCLE I WAS READY TO BUY AND LONG BEHOLD A BUDDY OF MINES WHO IS A REALTOR PRESENTED ME THE DEAL AND LET ME MEET THE OWNER WE HAD A GREAT CONVERSATION AS HE TOURED THE PROPERTY WITH ME HE EXPLAINED HE HAD HIGHER OFFERS BUT BECAUSE HE SEE IM A YOUNG GUY DOING THE RIGHT THING HE REALLY WANTED TO SELL IT TO ME AND THE REST IS HISTORY !