Are your thoughts based on experience and research in this area or based on a gut reaction?

I know there is surety bond process and there a a few companies that appear to offer a service (Like Rhino)Furnished Finder has a new feature called Worry Free Waivers but when I tried  to better understand their process, it was clear they have not done a good job of vetting this out. 

Start with BiggerPockets Ultimate Beginners Guide (free).

Does anyone have experience doing this, and know how to go about it?

Has anyone transitioned from a construction manager role with a large company to developing real estate on their own.What has that experience been like?

What experience does he have in real estate or in selecting investments in his IRA?

Once you get done to that level experience really helps, visiting the area or having someone that knows the area, really helps as well. 

You can open these accounts for free with various financial institutions. 

What has been your experience and do you manage with a property manager or self manage ?

I have experience with Quickbooks Online, and looking to learn to use Appfolio as I have heard that is a common software tool used for managing the books for REI.