I'd pay off the debt.I paid off $87k in consumer debt and the payments I no longer have to make help propel me to complete freedom.When I was getting out of debt, my plow-back (re-savings rate) was huge and I saved my money back much faster than anticipated.My guess is you will buckle down and re-save the $37k more quickly than you think.  

But our fear of not succeeding propelled us to overcome that.

Oncarrot / Lead propeller or Wix/squarespacae or Wordpress?

He might even want to go visit the property more if he thinks he can put in a competitive bid, get introduced to investors through it, and propel his business forward.  

No matter how easy it is, I still want to get it because I see it as a tool that will help me propel in my career. 

Play it somewhat safe, but at the end of the day, only action will propel you to actual investor status.

Investor Carrot or Lead Propeller, and why?

At the age of 64, too often I reflect back on years of missed opportunity to propel my career forward....if I discovered and honed my passion early on and moved forward with a laser-beam like "focus". 

Which essentially seems to be the best way to propel myself into a great future (in terms of REI) by eliminating one of my biggest spending buckets (living expenses). 

Rental income will certainly propel you above and beyond your peers as you start out low on the totem pole with an airline.