And those that are tasked with working with them daily and in the trench's

Thank you, Taylor Given your unique circumstances as a professional athlete who may not know where you will be located in the future, a fix and flip strategy may be a good option to consider.

You need a good tax strategist that understands these very unique twists to owning STRs. 

@Rebecca BuschNot an easy task to find a great real estate centric tax advisor and certainly won't be cheap.Jon Bock, CPA/PFS

I'd ping my real estate attorney and ask, esp. since its a unique situation

Recovering for lost opportunity in any endeavor let alone real estate is  deemed speculative and an even more difficult task. 

I have the impression like you that they all create these type of unique structure to tell you we are your only savior and the only person who can protect you after paying 1000$ and 1000$ of dollars.Would you mine sharing what type of structure you have find to be good for people who start?

Your situation is unique and presents an exciting opportunity for your retirement planning.Given your aim to maximize your monthly income to supplement your CalSTRS retirement fund, and your desire to continue investing in properties post-retirement, here are a few suggestions:Assess Your Risk Tolerance: Transitioning from California properties to Indiana duplexes involves a shift in market dynamics and possibly different risk profiles.

Your background as a corporate chef brings a unique perspective, and I'm sure your skills and dedication will translate well into the real estate industry.

The coursework can be done online and the number of hours you have to put in varies from 45-90.This is not an extremely difficult task.