Apart from having trouble finding his way into the cool hide (remember snakes don't use vision very well- they tend to learn their way around using scent & by feel), it might be that his cool hide actually feels "bigger" inside to him than the space he wedges himself into behind it. What he's doing is similar to what snakes do in the wild- squeezing into rock crevices to hide. They like to feel wedged-in, & it's possible his hides feel too big to him. If that's the case, trying wadding some paper into the hide to make it feel more snug.
I've lived with many snakes for many years, & believe me, they don't read the training manuals.You'd think they'd show some gratitude after we spend so much money buying equipment to heat & regulate the temperatures safely in their enclosures, but no-o-o-o.
It appears to me that sometimes they deliberately slow down their digestion by staying on the cool side instead of heading for the warmth- my hunch (& observation) is that when the meal feels "large" to them, they slow their digestion so as not to overwhelm their GI tract, or perhaps to better digest & benefit from the nutrients? As long as they have options & 'get the job done', don't worry about it- they probably know what they're doing, even if we don't.
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