However, if I let go of my fear, realistically in the foreseeable future the risk of losing them is pretty small.

The experience I have had with this contractor has turned into the poster child of investors fears of working with a contractor.  

I know a lot of people have fears about becoming a landlord, but it really hasn't been my experience that the tenants have been too bad (knock on wood).

This seems to cut into your fear of the unknown regarding the housing market. 

Better to keep those separate.There is a way to transfer property to LLC officially. https://www.biggerpockets.com/member-blogs/12249/86026-transfer-property-to-llc-without-fearing-due-on-sale Agree with Josh's cautions!

The fear of a deal failing is hard to overcome, but getting out and doing it is where you start to see if this is really what you want to do. 

I have a friend who is willing to help out but he is skittish about being named on the lease as he fears it might legally bind him to something.  

Super valuable.I would add that the fear of a pending recession should not take anyone out of the game.

Yes, I am fearful finding any tenants during the winter months.

This sounds easier than it is because you have to be aware of the current climate & laws but not to the point you let "what if" scenarios based in heavy part on the ratings draw of panic / fear headlines.