As others have mentioned on here, every person's tax situation is unique and answers are not easily given over the internet and can often be incorrect. 

., etc. is going to make every property unique, but it would be great to come up with a rough rule of thumb that will allow a conservative estimate.

for a unique deal like this they might be more open, considering finding funding isn't as straight forward. just also be sure you have a backup plan for this property... what if they don't renew their lease at the end?

Each situation is unique, so your strategy depends on various factors.

Very unique group here, glad to be a part of it - I think you will be too!  

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. 

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?

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

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.