Has anyone done something like this before and has insight/tips/advice?

It can help build some incredible relationships and really learn some great tips from the pros!

Also any tips for automating this as much as possible and how to protect the property financially and property management would be appreciated.I ALMOST understand the rental arbitrage strategy if building a company scaling with say 30 + units and looking for high short term cash flow.  

A real estate lawyer can help you navigate the specifics, including ensuring you don’t inadvertently trigger any unintended tax consequences.A few tips to consider:Check with your mortgage lender: If there’s a loan on the property, transferring it to an LLC could violate the loan’s due-on-sale clause.

If police smell it they may be able to investigate further.

Do you have any tips on how to approach and structure deals with private lenders for scaling?

In hot markets, some wholesalers and investors use 80-85% of ARV (minus repairs) instead of the typical 70% to stay competitive.A few tips:1.

Investigate what (if any) additional fees that they charge for handling evictions, and find out whether they go to small-claims themselves, or hire an attorney.

That's not even the tip of the iceberg; it's so far away.

Feel free to ask if you’d like more tips on what to look for in a PM.