It helps the property manager safeguard themself against an owner who did a bad brrr to save money then think they should have the property manager basically be a gc for the 20% of work done wrong. 

Like it or not the physiological aspect of real estate is real.However putting in some safeguards mentally go a long way. 

He is with Safeguard advisors.

While complying with legal requirements is essential, going beyond and implementing additional safety measures is a proactive approach to safeguarding your pool area for residents and guests.

How should I approach this to safeguard the investment?

You must call upon the help of companies or contractors like safeguard, DhanInfo, etc. that routinely preserve and maintain the properties until they are sold.

You can imagine how much things can change within 365 years; it seems the trust should be built to evolve with the times and yet have strong safeguards built in. 

Can I safeguard myself in any way (if I proceed by giving the owner cash for first month rent + deposit)?

As an update for those interested in STR or Vacation Rentals in the Poconos, our rental alliance in the Poconos has reached a number of early milestones:PoconosVrO has received support and assistance from the Pocono Mountains Visitors Bureau (PMVB), our last meeting outlined a one day conference in March of 2024, at the end of the ski season.PoconosVRO has held several educational/professional development sessions and now have two corporate sponsors - thanks NoiseAware and Safeguard Insurance.  

But these are sector specific.All these industries are now trying to safe guard themselves.