Congrats to you and your son Rsquared. Went through the same challenges being a mentor, after my son's first year we bagged the ground blinds and I bought a few of the Walmart 15ft two man stands.
Made it a bit easier, him being able to see more of his surroundings kept his attention longer and the shooting rail freed up one of my hands from the shooting stick. I put double lifelines on every setup so he was attached from the time he started up the tree till the hunt was over.
I was concerned about deer seeing us in bigger stands but so far we have not been busted by a single deer in those set ups over the past 5 years.