A couple of days before my girl's most recent shed, she was miserable. She was a horrible color, and her eyes were very cloudy. He body felt strange to the touch, and she moved poorly. I had been out of town and didn't mess with her at first. The next day, I soaked her in warm water for about twenty minutes. She seemed to feel a little better, and I held her for a few minutes. She still wasn't happy. I may have soaked her again the following day, but she shed either that day or the following day. Once she'd shed, she was a couple of inches longer. I guess if my skin were three inches too short for my body, I'd be miserable as well. I'd be particularly miserable if three inches were almost 20% of my lenght.
If you're feeding your guy more regularly than the previous owner was, he may have gained weight and needs a bigger skin to accomodate his greater bulk. If so, he'd likely be miserable and lethargic as well. I'm sure he'll feel better after he's shed.
I don't know enough to know whether soaking is really a good idea, but I'd soak mine. I also spray my snakes with Vita-Spray and may try some Shed-Ease in the future. Again, I don't know what most keepers think about these products. I suspect that many people here have too many snakes to give each of them a massage every couple of days.
Bill
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It's not how many snakes you have. It's how happy and healthy you can keep them.