I sent her the check for returned security deposit by certified mail to a P.O. box she provided me.

I hope this can inspire some people and provide any kind of help.

Innovation and providing better services are what it's all about.Quote from @Tim Baldwin: Alex, it's a great question.

However, you do need to handle this situation carefully, make sure you follow a standard screening process to avoid any Fair Housing Act violations.I'm honestly not even sure if you can initiate the conversation with the parole officer, if they reach out to you, or the tenant provides the info and offers the opportunity to call them, that's a different story.Make sure you apply the same screening criteria you use for all potential tenants. 

You can easily do this on a spreadsheet, and it will take less time to track than finding and learning new software.

I am a very small fish in a huge pond, but the impact of my first BPCON has provided me with an even stronger sense of community built into my personal portfolio.

I provide property management for Gulf Coast STRs.  

Find out their requirements to fund a construction loan and their terms to provide a permanent loan after construction.

We have all of those parameters pretty well laid out but are both pretty confused on the best way for me to give him the money and for him to provide the return of my money. 

Those would provide some safe harbor since they are government issued docs