There may be many things to be factored into your decision... price is one, anther one is what is how you power your devices, yet another one is your wifi infrastructure.
esp32 - Espruino on ESP32 is a multi-core (duo core) processor and has also more memory resources. About how far the port of Espruino - that includes all the support incl HTTPS - has been achieved, you have to track down the conversations in the forum... I know that @Wilberforce, @JumJum, @Kolban (and others) have worked on its guts, and I have nowhere read that SSL would not be supported. From conversation Writing an SSL HTTPS web server ... I read that connecting with https to a server in the net is there, but not running a https listening server on ESP32.
Looking up some more info about SLL and ESP8266, I came across this nice youtube
and follow-up presentation. It talks about the space issue creating functions involved in SSL communication. Going to a single, defined server gives some relieve, and may be an option to go with less resource...
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