Certain clients started to fail after certificate renewal, while others didn't

Same for #2

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Ok then it has something to do with the chain now being different (longer than before) and Tomcat not being able to handle the new chain.

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I can't say for sure, but I don't think Tomcat is unable to handle a chain because it's long. Besides, the problem is not appearing on browsers and many hardware devices, only for one type, so it discards in my opinion that it's about Tomcat.
It makes sense to me that the long chain is a handicap for ESP01 device, that is the one with less resources among the ones I'm dealing with.