It was a very sad, fulfilling and humbling experience.

I know of several Agents and Brokers who have done exactly that, bought a property after the Listing of that property expired.In fact, I know several Sellers who had sold their properties to their Brokers, none of them have complained and one really appreciated the fact that she had sold it at all.Do you personally have knowledge of a Seller complaining that their Broker bought their property and somehow did not fulfill their Marketing obligation beforehand?

Welcome to BP Account Closed as an attorney who will fulfill all your real estate needs.

I am a life long resident and have seen many positive changes to the city.

If not worst case scenario you pay off your debt and have life long relationships and connections already established because you didn't just sit on your hands for years.

He probably then had the end buyer put down the earnest money, thus fulfilling his promissory note.

Literally if you run your business right you can do everything involved with this situation via email and phone calls from your home/office, just to ensure all of your moving-parts are doing fulfilling their roles.

We both have had great careers and always had everything we needed, but something about getting up every morning and going to a job that is not fulfilling really eats at me. 

Then find a particular need in that space and challenge yourself to fulfill that need by designing a new app or helping someone to improve an existing app in the space. 

.#3  Pursue life-long learning.